A NOVEL AND HIGHLY EFFICIENT DESYMMETRIZATION OF A MESO-ANHYDRIDE BY A CHIRAL GRIGNARD-REAGENT

被引：30

作者：

REAL, SD

KRONENTHAL, DR

WU, HY

机构：

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 50期

关键词：

D O I：

10.1016/S0040-4039(00)61451-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of the chiral oxazolidine Grignard 3c to anhydride 1, followed by in situ NaBH4 reduction and acid hydrolysis, provides aldehyde 2 in greater than 98% enantiomeric excess.

引用

页码：8063 / 8066

页数：4

共 10 条

[1] STEREOCHEMISTRY .60. KINETIC CONTROL OF ASYMMETRIC INDUCTION DURING OXAZOLIDINE FORMATION FROM (-)-EPHEDRINE AND AROMATIC-ALDEHYDES
AGAMI, C
RIZK, T
[J]. TETRAHEDRON, 1985, 41 (03) : 537 - 540
[2] CHIRAL AMINAL TEMPLATES .4. CHIRAL ARYL METALLIC REAGENTS - REACTIONS WITH ALDEHYDES
COMMERCON, M
MANGENEY, P
TEJERO, T
ALEXAKIS, A
[J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (05) : 287 - 290
[3] CHIRAL ARYL GRIGNARD REAGENTS-GENERATION AND REACTIONS WITH CARBONYL-COMPOUNDS
KAINO, M
ISHIHARA, K
YAMAMOTO, H
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (11) : 3736 - 3738
[4] HIGHLY ENANTIOSELECTIVE REDUCTION OF MESO-1,2-DICARBOXYLIC ANHYDRIDES
MATSUKI, K
INOUE, H
TAKEDA, M
[J]. TETRAHEDRON LETTERS, 1993, 34 (07) : 1167 - 1170
[5] THROMBOXANE RECEPTOR ANTAGONIST BMS-180291 - A NEW PRECLINICAL LEAD
MISRA, RN
BROWN, BR
SHER, PM
PATEL, MM
HALL, SE
HAN, WC
BARRISH, JC
FLOYD, DM
SPRAGUE, PW
MORRISON, RA
RIDGEWELL, RE
WHITE, RE
DIDONATO, GC
HARRIS, DN
HEDBERG, A
SCHUMACHER, WA
WEBB, ML
OGLETREE, ML
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1992, 2 (01) : 73 - 76
[6] PHYSICOCHEMICAL STUDY ON SOME SYNTHESIZED OXAZOLIDINE DERIVATIVES - DIFFERENTIATION OF DIASTEREOMERS
SOLIMAN, SA
ABDINE, H
ELNENAEY, S
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1975, 28 (01) : 49 - 56
[7] HIGHLY DIASTEREOSELECTIVE ALCOHOLYSIS OF SIGMA-SYMMETRICAL DICARBOXYLIC-ACID ANHYDRIDES USING 1-PHENYL-3,3-BIS(TRIFLUOROMETHYL)PROPAN-1,3-DIOL
SUDA, Y
YAGO, S
SHIRO, M
TAGUCHI, T
[J]. CHEMISTRY LETTERS, 1992, (03) : 389 - 392
[8] TAKAHASHI H, 1992, SYNTHESIS-STUTTGART, P681
[9] THOTTATHIL J, 1988, Patent No. 4743697
[10] NONENZYMATIC ASYMMETRIC TRANSFORMATIONS INVOLVING SYMMETRICAL BIFUNCTIONAL COMPOUNDS
WARD, RS
[J]. CHEMICAL SOCIETY REVIEWS, 1990, 19 (01) : 1 - 19

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