Synthesis of 4-Amino-5 H -1,2-oxathiole 2,2-Dioxides by Cyclization of...
1
of NaClO (0.11 mL of a 2.0 M aqueous solution, 0.22 mmol), saturated aqueous NaHCO3 (0.8 mL), and brine (1.5 mL) dropwise over 45 min. The mixture was stirred for 1 h at 0 °C and then for 20 min at 20 °C. The progress of the reaction was carefully monitored by TLC. The aqueous phase was extracted with CH2Cl2, and the combined extracts were washed with saturated aqueous NaHCO3 and brine, dried (Na2SO4), and filtered. Evaporation of the solvent and flash chromatography of the crude residue gave 9 (12.0 mg, 61%); Rf ) 0.50 (50% EtOAc:petroleum ether); mp 94-96 °C; [R] 25 D )-7.16° (c 0.72, CHCl3). Literature: 95-96 °C; [R] 25 D )-7.36° (c 1.44, CHCl3). 1 H NMR (CDCl3) was identical to previously prepared 9. 6b HRCIMS calcd for C21H39O4 (M + H) + 355.2848. Found 355.2848. Acknowledgment. This investigation was sup- ported in part by a “Research Centers in Minority Institutions” award, RR-03037, from the Division of Research Resources, National Institutes of Health. Supporting Information Available: 1 H and 13 C NMR spectra of (4E)-8-(benzyloxy)-4-octenal, 1, 4, 5-E,E, 5-Z,E, 6, 6-bis-MTPA ester, (()-6-bis-MTPA ester, 7, 8, and 9 (28 pages). This material is contained in libraries on microfiche, im- mediately follows this article in the microfilm version of the journal, and can be ordered from the ACS; see any current masthead page for ordering information. JO961367I Additions and Corrections Vol. 61, 1996 Fe ´ lix Busque ´ , Pedro de March,* Marta Figueredo, Josep Font,* Montserrat Monsalvatje, Albert Virgili, A Ä ngel A Ä lvarez-Larena, and Juan F. Piniella. Diastereofacial Selectivity in the Cycloaddition of Nitrones to (E)-γ-Oxygenated R,-Unsaturated Esters. Page 8578. Charts 1 and 3. Formula 6 in Chart 1 and formulae 11a,b and 17a-d in Chart 3 should have the opposite absolute configuration at the chiral center. Corrected structures are as follows: JO9740305 S0022-3263(97)04030-9 Published on Web 02/24/1998 Vol. 62, 1997 Nobuya Katagiri,* Masahiro Takebayashi, Hideaki Kokufuda, Chikara Kaneko, Kouichi Kanehira, and Masahiro Torihara. Efficient Synthesis of Carbovir and Its Congener via π-Allylpalladium Complex Fomation by Ring Strain-Assisted C-N Bond Cleavage. Page 1580. Reference 3a should read as follows: Daluge, S. M.; Good, S. S.; Martin, M. T.; Tibbels, S. R.; Miller, W. H.; Averett, D. R.; Clair, M. S. St.; Ayers, K. M. In Abstracts of the 34th interscience Conference on Antimicrobial Agents and Chemotherapy; American So- ciety for Microbiology: Washington, DC, 1994; Abstr. I6, p 7. JO974033H S0022-3263(97)04033-4 Published on Web 02/24/1998 Naoki Asao, Takashi Shimada, Tomoko Sudo, Naofumi Tsukada, Kazuhiko Yazawa, Young Soo Gyoung, Tadao Uyehara, and Yoshinori Yamamoto*. Highly Diastereose- lective Conjugate Addition of Lithium Dialkylamides to R,- Unsaturated Esters Having a Chiral Center at the γ-Position. Page 6282. The following acknowledgment should be added. Acknowledgment. Prof. Y. S. Gyoung acknowledges financial support from the Korean Science and Engineer- ing Foundation (956-0300-001-2). JO9740352 S0022-3263(97)04035-8 Published on Web 02/24/1998 La ´ szlo ´ Posza ´ va ´ cz and Gyula Simig*. Synthesis of 4-Amino- 5H-1,2-oxathiole 2,2-Dioxides by Cyclization of Cyanohydrin Mesylates. New Routes to -Amino and -Keto Sulfonic Acids. Page 7021, column 2, 15th line. With respect to the sentence “To the best of our knowledge, compounds 3 are the first 4-amino substituted 1,2-oxathioles, which may find interesting applications in organic synthesis.”, we regret our failure to mention the pioneering studies reported by Dr. Marı ´a-Jose ´ Camarasa and his co-workers on the cyclization of cyanohydrin mesylates to 4-amino substituted 1,2-oxathioles. References are given below: (1) Calvo-Mateo, A.; Camarasa, M. J.; Dı ´az-Ortı ´z, A.; de las Heras, F. G. J. Chem. Soc., Chem. Commun. 1988, 1114. (2) Pe ´rez-Pe ´rez, M. J.; Balzarini, J.; Hosoya, M.; De Clercq, E.; Camarasa, M. J. BioMed. Chem. Lett. 1992, 2, 647. (3) Camarasa, M. J.; Pe ´rez-Pe ´rez, M. J.; San-Fe ´lix, A.; Balzarini, J.; De Clercq, E. J. Med. Chem. 1992, 35, 2721. JO974034+ S0022-3263(97)04034-6 Published on Web 03/03/1998 2052 J. Org. Chem., Vol. 63, No. 6, 1998 Additions and Corrections
Transcript of Synthesis of 4-Amino-5 H -1,2-oxathiole 2,2-Dioxides by Cyclization of...
of NaClO (0.11 mL of a 2.0 M aqueous solution, 0.22 mmol),saturated aqueous NaHCO3 (0.8 mL), and brine (1.5 mL)dropwise over 45 min. The mixture was stirred for 1 h at 0 °Cand then for 20 min at 20 °C. The progress of the reaction wascarefully monitored by TLC. The aqueous phase was extractedwith CH2Cl2, and the combined extracts were washed withsaturated aqueous NaHCO3 and brine, dried (Na2SO4), andfiltered. Evaporation of the solvent and flash chromatographyof the crude residue gave 9 (12.0 mg, 61%); Rf ) 0.50 (50%EtOAc:petroleum ether); mp 94-96 °C; [R]25D ) -7.16° (c0.72, CHCl3). Literature: 95-96 °C; [R]25D ) -7.36° (c 1.44,CHCl3). 1H NMR (CDCl3) was identical to previously prepared9.6b HRCIMS calcd for C21H39O4 (M + H)+ 355.2848. Found355.2848.
Acknowledgment. This investigation was sup-ported in part by a “Research Centers in MinorityInstitutions” award, RR-03037, from the Division ofResearch Resources, National Institutes of Health.
Supporting Information Available: 1H and 13C NMRspectra of (4E)-8-(benzyloxy)-4-octenal, 1, 4, 5-E,E, 5-Z,E, 6,6-bis-MTPA ester, (()-6-bis-MTPA ester, 7, 8, and 9 (28 pages).This material is contained in libraries on microfiche, im-mediately follows this article in the microfilm version of thejournal, and can be ordered from the ACS; see any currentmasthead page for ordering information.
JO961367I
Additions and CorrectionsVol. 61, 1996
Felix Busque, Pedro de March,* Marta Figueredo,Josep Font,* Montserrat Monsalvatje, Albert Virgili,AÄ ngel AÄ lvarez-Larena, and Juan F. Piniella. DiastereofacialSelectivity in the Cycloaddition of Nitrones to (E)-γ-OxygenatedR,â-Unsaturated Esters.
Page 8578. Charts 1 and 3. Formula 6 in Chart 1 andformulae 11a,b and 17a-d in Chart 3 should have theopposite absolute configuration at the chiral center.Corrected structures are as follows:
JO9740305
S0022-3263(97)04030-9Published on Web 02/24/1998
Vol. 62, 1997
Nobuya Katagiri,* Masahiro Takebayashi, HideakiKokufuda, Chikara Kaneko, Kouichi Kanehira, andMasahiro Torihara. Efficient Synthesis of Carbovir and ItsCongener via π-Allylpalladium Complex Fomation by RingStrain-Assisted C-N Bond Cleavage.
Page 1580. Reference 3a should read as follows:Daluge, S. M.; Good, S. S.; Martin, M. T.; Tibbels, S. R.;Miller, W. H.; Averett, D. R.; Clair, M. S. St.; Ayers, K.M. In Abstracts of the 34th interscience Conference onAntimicrobial Agents and Chemotherapy; American So-ciety for Microbiology: Washington, DC, 1994; Abstr. I6,p 7.
JO974033H
S0022-3263(97)04033-4Published on Web 02/24/1998
Naoki Asao, Takashi Shimada, Tomoko Sudo, NaofumiTsukada, Kazuhiko Yazawa, Young Soo Gyoung, TadaoUyehara, and Yoshinori Yamamoto*. Highly Diastereose-lective Conjugate Addition of Lithium Dialkylamides to R,â-Unsaturated Esters Having a Chiral Center at the γ-Position.
Page 6282. The following acknowledgment should beadded.
Acknowledgment. Prof. Y. S. Gyoung acknowledgesfinancial support from the Korean Science and Engineer-ing Foundation (956-0300-001-2).
JO9740352
S0022-3263(97)04035-8Published on Web 02/24/1998
Laszlo Poszavacz and Gyula Simig*. Synthesis of 4-Amino-5H-1,2-oxathiole 2,2-Dioxides by Cyclization of CyanohydrinMesylates. New Routes to â-Amino and â-Keto Sulfonic Acids.
Page 7021, column 2, 15th line. With respect to thesentence “To the best of our knowledge, compounds 3 arethe first 4-amino substituted 1,2-oxathioles, which mayfind interesting applications in organic synthesis.”, weregret our failure to mention the pioneering studiesreported by Dr. Marıa-Jose Camarasa and his co-workerson the cyclization of cyanohydrin mesylates to 4-aminosubstituted 1,2-oxathioles. References are given below:(1) Calvo-Mateo, A.; Camarasa, M. J.; Dıaz-Ortız, A.;
de las Heras, F. G. J. Chem. Soc., Chem. Commun. 1988,1114.(2) Perez-Perez, M. J.; Balzarini, J.; Hosoya, M.; De
Clercq, E.; Camarasa, M. J. BioMed. Chem. Lett. 1992,2, 647.(3) Camarasa, M. J.; Perez-Perez, M. J.; San-Felix, A.;
Balzarini, J.; De Clercq, E. J. Med. Chem. 1992, 35, 2721.
JO974034+
S0022-3263(97)04034-6Published on Web 03/03/1998
2052 J. Org. Chem., Vol. 63, No. 6, 1998 Additions and Corrections
