Correction. Intramolecular Aminolysis of Esters. O-Acetylserine and γ-Esters of Glutamic Acid

1
5460 J. Org. Chem., Vol. 46, No. 26, 1981 Additions and Corrections Clayton H. Heathcock,* Charles T. White, James Jeffrey Morrison, and Don VanDerveer. Acyclic Stereoselection. 11. Double Stereodifferentiation as a Method for Achieving Superior Cram’s Rule Selectivity in Aldol Condensations with Chiral Al- dehydes. Page 1300. The octant projections depicted in Figures 3-5 in this paper are incorrect, as is the discussion of these figures which is found on page 1300, column 1. These figures, and the discussion of them, should be disregarded. At this time it is not clear whether or not the Cotton effects shown by aldols 34 and 35 can be ra- tionalized in terms of preferred solution conformations. However, the experimental observation is still true that aldol 34, with the (aR,PR) configuration, shows a more positive Cotton effect than ketone 6, while aldol 35, with the (aS,pS) configuration shows a more negative Cotton effect than 6. Michael Caswell, Rama K. Chaturvedi, Stuart M. Lane, Bina Zvilichovsky, and Gaston L. Schmir.* Intramolecular Ami- nolysis of Esters. 0-Acetylserine and ?-Esters of Glutamic Acid. Page 1585. The last line of the abstract should read: “in the mechanisms of the intra- and intermolecular aminolysis of esters of weakly acidic alcohols”. Stewart W. Schneller* and William J. Christ. Synthesis of lin-Benzofervenulin, lin-Benzotheophylline, and lin-Benzocaffeine. Page 1700. Formula numbers 11 and 19 were omitted for structure shown at top left of column 2: 11, R = H; 19, R = CH3. D. S. Kemp,* Frank Vellaccio, and Neal Gilman. Structure of Anhydroacetylsalicylamide. Page 1806. Column 1, line 20-24 should read “to structure 8 and 9. Structure 7, which has two such functions, is therefore incompatible with the proton NMR spectrum and can be excluded on this basis. The availability of 250-MH2 ‘H spectra for 1, 4, and 12 allows con-”. H. Kwart,* T. J. George, A. G. Horgan, and Y. T. Lin. The Transition State in the Carbonyl-Forming Elimination Reaction of Alkyl Nitrates. Page 1971. Second column, line 3 (beneath Figure 1) reads -0.9 A as the width of the reaction barrier. The correct value is 1.32 A. Palaniappan Nanjappan, Kondareddiar Ramalingam,* Nagichettiar Satyamurthy, and Kenneth Darrell Berlin.* Studies on the Conformation of Some Substituted 4-Selenanols. Page 2542. Table I, column 4: the compound numbers should appear on the same line as the values, Le., 63 (la), 53 (IC), 75 (3b). Page 2546. Line 14 from bottom reads as follows: “Calcd for C13H120C1: C, 71.07; H, 5.51”. The correct numbers are as follows: “Calcd for Cl3HI30C1: C, 70.75; H, 5.89”. Theodore J. Nitz, Elizabeth M. Holt, Byron Rubin, and Charles H . Stammer . * N- [ (Carbobenzyl) oxy] - AE- phen ylalanine Ethyl Ester. Page 2667. In our recent publication on the synthesis and stability of N-[ (carbobenzy1)oxyl-AE-phenylalanine ethyl ester, reference to the prior work of D. Hoppe [Angew.Chem., Znt. Ed. Engl., 12,656 (1973); Chem. Ber., 109,3062 (1976)] on this com- pound was inadvertently omitted. We stand corrected. Stephen K. Taylor,* Gay L. Lilley, Kevin J. Lilley, and Patricia A. McCoy. Highly Stereoselective Friedel-Crafts Al- kylations via Transannular Reactions. Pages 2709-2712. All compounds named as (1R*,4R,4aR,8aR)-decahydro-4-aryl-l-naphthols should be des- ignated as (1R*,4R*,4aR*,8aR*)-decahydro-4-aryl-l-naphtols. A journal editor incorrectly dropped the asterisks. Page 2711. Column 2. Compounds 2 and 3 should be named as @-tolyl)and (0-tolyl) compounds, respectively (instead of toluyl compounds). Mansour A. Makhlouf and Bruce Rickborn.* 1-Methoxy- isobenzofuran: Formation from 1,3-Dihydro-l,l-dimethoxyiso- benzofuran. Page 2737. Structure 26 should be reformulated as shown here, 26 based on analogy with the work of L. Contreras, D. B. MacLean, R. Faggiani, and C. J. L. Lock, Can. J. Chem., 59,1247 (1981). Evidence supporting this structure consists of the data given previously, and close similarity of the proton-coupled 13CNMR spectrum (CDC13) with that described by MacLean for the cor- responding ethyl ester, in particular a triplet at 33.91 ppm for the benzylic methylene carbon. Page 2738. Column 2, line 22: the NMR signals for the methoxy groups of 14 (CC1.J should be shown as 3.74,3.67, and 3.60 ppm. Palanisamy Arjunan, K. Darrell Berlin,* Charles L. Barnes, and Dick van der Helm.* Syntheses and a Conformational Study of Certain Selected 3-0xa-7-ababicyclo[3.3.l]nonan-9-ones. Single-Crystal X-ray Diffraction Analysis of 6,8-Bis(2-chloro- phenyl)-3-oxa-7-azabicyclo[3.3.l]nonan-9-one. Page 3197. Left column, line 14, reads as follows: “However, ketones Ig and If‘, and should read as follows: “However,ketones lg and Ih”. Page 3197. Right column, formula 1: the atom between 1 and 3 is labeled “5”: it should be “2”. Barry D. Dean and William E. Truce.* Oxidative Conversions of Sulfene Cycloadducts from Azaheptafulvenes and from Tropone to 1,2-Disubstituted Indoles and 2-arylbenzofurans, Respectively. Page 3575. Scheme I: right-hand structure of middle line of the scheme has too many double bonds. The correct structure is as follows: *- Y Marek Chmielewski, James N. BeMiller,* and Douglas Pat Cerretti. Reverse Anomeric Effect of the Carbamoyl Group of 2,6-Anhydroheptonamides. Page 3905. Table I, last column. Values 9 and 0 should be replaced with 91 and 100, respectively. Page 3906. Column 2, lines 32-36 should read as follows: “In this way it was found that, in CDC13 solution, compounds 2, 6, 7, 10, 12, and 14 (a-D-glUC0, a-D-gdacto, a-D-manno, and a-D-talo configurations were in the 2C5 conformation, and compounds 3, 5, 8, 11, 13, and 15 having the /3-D configuration existed only in the 5C2conformation”.

Transcript of Correction. Intramolecular Aminolysis of Esters. O-Acetylserine and γ-Esters of Glutamic Acid

Page 1: Correction. Intramolecular Aminolysis of Esters. O-Acetylserine and γ-Esters of Glutamic Acid

5460 J . Org. Chem., Vol. 46, No. 26, 1981 Additions and Corrections

Clayton H. Heathcock,* Charles T. White, James Jeffrey Morrison, and Don VanDerveer. Acyclic Stereoselection. 11. Double Stereodifferentiation as a Method for Achieving Superior Cram’s Rule Selectivity in Aldol Condensations with Chiral Al- dehydes.

Page 1300. The octant projections depicted in Figures 3-5 in this paper are incorrect, as is the discussion of these figures which is found on page 1300, column 1. These figures, and the discussion of them, should be disregarded. At this time it is not clear whether or not the Cotton effects shown by aldols 34 and 35 can be ra- tionalized in terms of preferred solution conformations. However, the experimental observation is still true that aldol 34, with the (aR,PR) configuration, shows a more positive Cotton effect than ketone 6, while aldol 35, with the (aS,pS) configuration shows a more negative Cotton effect than 6.

Michael Caswell, Rama K. Chaturvedi, Stuart M. Lane, Bina Zvilichovsky, and Gaston L. Schmir.* Intramolecular Ami- nolysis of Esters. 0-Acetylserine and ?-Esters of Glutamic Acid.

Page 1585. The last line of the abstract should read: “in the mechanisms of the intra- and intermolecular aminolysis of esters of weakly acidic alcohols”.

Stewart W. Schneller* and William J. Christ. Synthesis of lin-Benzofervenulin, lin-Benzotheophylline, and lin-Benzocaffeine.

Page 1700. Formula numbers 11 and 19 were omitted for structure shown at top left of column 2: 11, R = H; 19, R = CH3.

D. S. Kemp,* Frank Vellaccio, and Neal Gilman. Structure of Anhydroacetylsalicylamide.

Page 1806. Column 1, line 20-24 should read “to structure 8 and 9. Structure 7, which has two such functions, is therefore incompatible with the proton NMR spectrum and can be excluded on this basis. The availability of 250-MH2 ‘H spectra for 1, 4, and 12 allows con-”.

H. Kwart,* T. J. George, A. G. Horgan, and Y. T. Lin. The Transition State in the Carbonyl-Forming Elimination Reaction of Alkyl Nitrates.

Page 1971. Second column, line 3 (beneath Figure 1) reads -0.9 A as the width of the reaction barrier. The correct value is 1.32 A.

Palaniappan Nanjappan, Kondareddiar Ramalingam,* Nagichettiar Satyamurthy, and Kenneth Darrell Berlin.* Studies on the Conformation of Some Substituted 4-Selenanols.

Page 2542. Table I, column 4: the compound numbers should appear on the same line as the values, Le., 63 (la), 53 (IC), 75 (3b).

Page 2546. Line 14 from bottom reads as follows: “Calcd for C13H120C1: C, 71.07; H, 5.51”. The correct numbers are as follows: “Calcd for Cl3HI30C1: C, 70.75; H, 5.89”.

Theodore J. Nitz, Elizabeth M. Holt, Byron Rubin, and Charles H . Stammer . * N- [ (Carbobenzyl) oxy] - AE- phen ylalanine Ethyl Ester.

Page 2667. In our recent publication on the synthesis and stability of N-[ (carbobenzy1)oxyl-AE-phenylalanine ethyl ester, reference to the prior work of D. Hoppe [Angew. Chem., Znt. Ed. Engl., 12,656 (1973); Chem. Ber., 109,3062 (1976)] on this com- pound was inadvertently omitted. We stand corrected.

Stephen K. Taylor,* Gay L. Lilley, Kevin J. Lilley, and Patricia A. McCoy. Highly Stereoselective Friedel-Crafts Al- kylations via Transannular Reactions.

Pages 2709-2712. All compounds named as (1R*,4R,4aR,8aR)-decahydro-4-aryl-l-naphthols should be des- ignated as (1R*,4R*,4aR*,8aR*)-decahydro-4-aryl-l-naphtols. A journal editor incorrectly dropped the asterisks.

Page 2711. Column 2. Compounds 2 and 3 should be named as @-tolyl) and (0-tolyl) compounds, respectively (instead of toluyl compounds).

Mansour A. Makhlouf and Bruce Rickborn.* 1-Methoxy- isobenzofuran: Formation from 1,3-Dihydro-l,l-dimethoxyiso- benzofuran.

Page 2737. Structure 26 should be reformulated as shown here,

26

based on analogy with the work of L. Contreras, D. B. MacLean, R. Faggiani, and C. J. L. Lock, Can. J. Chem., 59,1247 (1981). Evidence supporting this structure consists of the data given previously, and close similarity of the proton-coupled 13C NMR spectrum (CDC13) with that described by MacLean for the cor- responding ethyl ester, in particular a triplet a t 33.91 ppm for the benzylic methylene carbon.

Page 2738. Column 2, line 22: the NMR signals for the methoxy groups of 14 (CC1.J should be shown as 3.74,3.67, and 3.60 ppm.

Palanisamy Arjunan, K. Darrell Berlin,* Charles L. Barnes, and Dick van der Helm.* Syntheses and a Conformational Study of Certain Selected 3-0xa-7-ababicyclo[3.3.l]nonan-9-ones. Single-Crystal X-ray Diffraction Analysis of 6,8-Bis(2-chloro- phenyl)-3-oxa-7-azabicyclo[3.3.l]nonan-9-one.

Page 3197. Left column, line 14, reads as follows: “However, ketones Ig and If‘, and should read as follows: “However, ketones lg and Ih”.

Page 3197. Right column, formula 1: the atom between 1 and 3 is labeled “5”: it should be “2”.

Barry D. Dean and William E. Truce.* Oxidative Conversions of Sulfene Cycloadducts from Azaheptafulvenes and from Tropone to 1,2-Disubstituted Indoles and 2-arylbenzofurans, Respectively.

Page 3575. Scheme I: right-hand structure of middle line of the scheme has too many double bonds. The correct structure is as follows: *- Y

Marek Chmielewski, James N. BeMiller,* and Douglas Pat Cerretti. Reverse Anomeric Effect of the Carbamoyl Group of 2,6-Anhydroheptonamides.

Page 3905. Table I, last column. Values 9 and 0 should be replaced with 91 and 100, respectively.

Page 3906. Column 2, lines 32-36 should read as follows: “In this way it was found that, in CDC13 solution, compounds 2, 6, 7, 10, 12, and 14 (a-D-glUC0, a-D-gdacto, a-D-manno, and a-D-talo configurations were in the 2C5 conformation, and compounds 3, 5, 8, 11, 13, and 15 having the /3-D configuration existed only in the 5C2 conformation”.