ENANTIOMERICALLY ENRICHED TERT-BOC-PROTECTED ALPHA-AMINOORGANOLITHIUMS - PREPARATION AND CONFIGURATIONAL STABILITY

被引:116
作者
CHONG, JM
PARK, SB
机构
[1] Guelph-Waterloo Centre for Graduate Work in Chemistry, Department of Chemistry, University of Waterloo, Waterloo, Ontario
关键词
D O I
10.1021/jo00034a007
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enantiomerically enriched t-BOC-protected alpha-aminoorganolithiums, generated by Sn-Li exchange, are configurationally stable at -95-degrees-C and may be trapped with complete retention of configuration.
引用
收藏
页码:2220 / 2222
页数:3
相关论文
共 48 条
[1]   ALPHA-LITHIOAMINE SYNTHETIC EQUIVALENTS FROM DIPOLE-STABILIZED CARBANIONS - THE TERT-BOC GROUP AS AN ACTIVATOR FOR ALPHA'-LITHIATION OF CARBAMATES [J].
BEAK, P ;
LEE, WK .
TETRAHEDRON LETTERS, 1989, 30 (10) :1197-1200
[2]   ALPHA-LITHIOAMINE SYNTHETIC EQUIVALENTS - SYNTHESES OF DIASTEREOISOMERS FROM THE BOC PIPERIDINES [J].
BEAK, P ;
LEE, WK .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) :2578-2580
[3]   ASYMMETRIC REDUCTION OF ACYLSTANNANES - PREPARATION OF ENANTIOMERICALLY ENRICHED ALPHA-ALKOXYSTANNANES [J].
CHAN, PCM ;
CHONG, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23) :5584-5586
[4]   N-METHYLAMINO ACIDS IN PEPTIDE-SYNTHESIS .5. SYNTHESIS OF N-TERT-BUTYLOXYCARBONYL, N-METHYLAMINO ACIDS BY N-METHYLATION [J].
CHEUNG, ST ;
BENOITON, NL .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (05) :906-910
[5]   PREPARATION OF ENANTIOMERICALLY ENRICHED ALPHA-HYDROXYSTANNANES VIA ENZYMATIC RESOLUTION [J].
CHONG, JM ;
MAR, EK .
TETRAHEDRON LETTERS, 1991, 32 (41) :5683-5686
[6]   CHIRAL DIPOLE-STABILIZED ANIONS - EXPERIMENT AND THEORY IN NONBENZYLIC SYSTEMS - 100-PERCENT STEREOSELECTIVE DEPROTONATION AND 2-ELECTRON VS SINGLE-ELECTRON TRANSFER IN THE CHEMISTRY OF LITHIUM AND COPPER PIPERIDINOOXAZOLINES [J].
GAWLEY, RE ;
HART, GC ;
BARTOLOTTI, LJ .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (01) :175-181
[7]  
GREHN L, 1988, SYNTHESIS-STUTTGART, P992
[8]   ASYMMETRIC-SYNTHESIS OF BENZOQUINOLIZIDINES - A FORMAL SYNTHESIS OF (-)-EMETINE [J].
GUILES, JW ;
MEYERS, AI .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) :6873-6878
[9]   PREPARATION AND C-ALKYLATION OF ENANTIOMERICALLY PURE S-PHENYL AZIRIDINECARBOTHIOATES - ON THE STRUCTURE OF SMALL-RING ESTER LITHIUM ENOLATES [J].
HANER, R ;
OLANO, B ;
SEEBACH, D .
HELVETICA CHIMICA ACTA, 1987, 70 (07) :1676-1693
[10]  
HIPPELI C, 1988, J ORG CHEM, V53, P3886