LEAD-TETRAACETATE CLEAVAGE OF CHIRAL PHENYLGLYCINOL DERIVED SECONDARY-AMINES WITHOUT RACEMIZATION

被引：30

作者：

MOKHALLALATI, MK ^{[1
]}

PRIDGEN, LN ^{[1
]}

机构：

[1] SMITHKLINE BEECHAM PHARMACEUT,DEPT SYNTHET CHEM,POB 1539,KING OF PRUSSIA,PA 19406

来源：

SYNTHETIC COMMUNICATIONS | 1993年 / 23卷 / 14期

关键词：

D O I：

10.1080/00397919308009866

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diastereomerically enriched N-(1,1-disubstituted methyl)(2-hydroxy-1'-phenylethyl)amines were oxidatively converted to enantiomerically enriched primary disubstituted methylamines in excellent yields without racemization, using an improved lead tetraacetate (LTA) procedure.

引用

页码：2055 / 2064

页数：10

共 18 条

[1] ASYMMETRIC-SYNTHESIS OF GAMMA,GAMMA-DIALKYL-GAMMA-AMINOBUTYRIC ACID ANALOGS AND 2,2-DISUBSTITUTED PYRROLIDINES - CONTROL OF STEREOCHEMISTRY IN AMINAL RING-OPENING BY VARYING THE EXTENT OF ALLYLIC 1,3-STRAIN [J].

BURGESS, LE ;

MEYERS, AI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (26) :9858-9859

[2]

CERVINKA O, 1973, COLLECT CZECH CHEM C, V38, P1159

[3] DIASTEREOSELECTIVE STRECKER SYNTHESIS USING ALPHA-PHENYLGLYCINOL AS CHIRAL AUXILIARY [J].

CHAKRABORTY, TK ;

REDDY, GV ;

HUSSAIN, KA .

TETRAHEDRON LETTERS, 1991, 32 (51) :7597-7600

[4] ENANTIOSELECTIVE SYNTHESIS OF PRIMARY AMINES VIA GRIGNARD ADDITIONS TO STEREOGENIC N-(ALPHA-PHENYL-BETA-(BENZYLOXY)ETHYL)NITRONES [J].

CHANG, ZY ;

COATES, RM .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3475-3483

[5]

GAWLEY RE, 1989, J ORG CHEM, V54, P5826

[6]

GRAF E, 1958, LIEBIGS ANN CHEM, V613, P111

[7] SYNTHESIS OF OPTICALLY-ACTIVE BETA-LACTAMS BY THE PHOTOLYTIC REACTION OF IMINES WITH OPTICALLY-ACTIVE CHROMIUM CARBENE COMPLEXES [J].

HEGEDUS, LS ;

IMWINKELRIED, R ;

ALARIDSARGENT, M ;

DVORAK, D ;

SATOH, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (03) :1109-1117

[8] A SIMPLE ASYMMETRIC-SYNTHESIS OF 2-SUBSTITUTED PYRROLIDINES FROM 3-ACYLPROPIONIC ACIDS [J].

MEYERS, AI ;

BURGESS, LE .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2294-2296

[9] ASYMMETRIC CONJUGATE ADDITIONS TO CHIRAL BICYCLIC LACTAMS - SYNTHESIS OF ARACEMIC TRANS-2,3-DISUBSTITUTED PYRROLIDINES [J].

MEYERS, AI ;

SNYDER, L .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) :3814-3819

[10] AN EFFICIENT ENANTIOMERIC 3 STEP SYNTHESIS OF BETA-AMINO ACIDS (ESTERS) [J].

MOKHALLALATI, MK ;

WU, MJ ;

PRIDGEN, LN .

TETRAHEDRON LETTERS, 1993, 34 (01) :47-50

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