OXIDATION OF ALPHA-AMINO ESTERS - ONE-STEP SYNTHESIS OF SULFENIMINES

被引:18
作者
GORDON, EM
PLUSCEC, J
机构
[1] Squibb Institute for Medical Research, New Jersey, Princeton
关键词
D O I
10.1021/jo01322a006
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
α-Amino esters (1) were oxidized to their corresponding sulfenimine derivatives (2) by mild treatment with ptoluenesulfenyl chloride in the presence of acid scavengers. Such amino acid derived sulfenimines are converted to α-keto esters by treatment with triphenylphosphine and silica gel. Oxidation of sulfenimines is discussed, including an example which gives rise to a dehydroamino acid residue. © 1979, American Chemical Society. All rights reserved.
引用
收藏
页码:1218 / 1221
页数:4
相关论文
共 16 条
[1]   HERSTELLUNG VON ALPHA-AMINOSAUREESTERN DURCH ALKOHOLYSE DER METHYLESTER [J].
BRENNER, M ;
HUBER, W .
HELVETICA CHIMICA ACTA, 1953, 36 (05) :1109-1115
[2]  
CAIRNS TL, 1955, ORGANIC SYNTHESES, V35, P99
[3]   CHEMISTRY OF SULFUR-NITROGEN BOND .13. NEW SYNTHESIS OF N-ALKYLIDENEARENESULFENAMIDES (SULFENIMINES) - ALKYLATION OF SULFENAMIDE ENOLATE EQUIVALENTS [J].
DAVIS, FA ;
MANCINELLI, PA .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (09) :1797-1800
[4]   CHEMISTRY OF SULFUR-NITROGEN BOND .7. REARRANGEMENT OF SULFENIMINES (S-ARYL THIOOXIMES) TO BETA-KETO SULFIDES - ATTEMPTED SYNTHESIS OF BENZO[B]THIOPHENES [J].
DAVIS, FA ;
SKIBO, EB .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (06) :807-811
[5]   CHEMISTRY OF SULFUR-NITROGEN BOND .6. CONVENIENT ONE-STEP SYNTHESIS OF SULFENIMINES (S-ARYL THIOOXIMES) [J].
DAVIS, FA ;
SLEGEIR, WAR ;
EVANS, S ;
SCHWARTZ, A ;
GOFF, DL ;
PALMER, R .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (16) :2809-2813
[6]   CHEMISTRY OF SULFUR-NITROGEN BOND .12. METAL-ASSISTED SYNTHESIS OF SULFENAMIDE DERIVATIVES FROM ALIPHATIC AND AROMATIC DISULFIDES [J].
DAVIS, FA ;
FRIEDMAN, AJ ;
KLUGER, EW ;
SKIBO, EB ;
FRETZ, ER ;
MILICIA, AP ;
LEMASTERS, WC ;
BENTLEY, MD ;
LACADIE, JA ;
DOUGLASS, IB .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (06) :967-972
[7]   CHEMISTRY OF SULFUR-NITROGEN BOND .9. TRANSMISSION OF ELECTRONIC EFFECTS IN N-ALKYLIDENEARENESULFENAMIDES, N-ALKYLIDENEARENESULFINAMIDES N-ALKYLIDENEARENESULFONAMIDES, AND ARENESULFENANILIDES [J].
DAVIS, FA ;
KAMINSKI, JM ;
KLUGER, EW ;
FREILICH, HS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (24) :7085-7091
[8]   CHEMISTRY OF SULFUR-NITROGEN BOND .14. ARENESULFENIC ACIDS FROM N-ALKYLIDENEARENESULFINAMIDES (SULFINIMINES) [J].
DAVIS, FA ;
FRIEDMAN, AJ ;
NADIR, UK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (09) :2844-2852
[9]  
DAVIS FA, 1974, J AM CHEM SOC, V96, P5000, DOI 10.1021/ja00822a055
[10]  
DAVIS FA, 1977, J ORG CHEM, V42, P399