(5R)-7,8/9,10-DI-O-ISOPROPYLIDENE-2,6-DIOXA-4-AZASPIRO[4,5]DECAN-3-ONE - A NEW CHIRAL SPIROOXAZOLIDIN-2-ONE DERIVED FROM D-(+)-GALACTOSE FOR USE IN ASYMMETRIC TRANSFORMATIONS

被引：25

作者：

BANKS, MR ^{[1
]}

BLAKE, AJ ^{[1
]}

CADOGAN, JIG ^{[1
]}

DAWSON, IM ^{[1
]}

GAUR, S ^{[1
]}

GOSNEY, I ^{[1
]}

GOULD, RO ^{[1
]}

GRANT, KJ ^{[1
]}

HODGSON, PKG ^{[1
]}

机构：

[1] BP INT LTD,SUNBURY RES CTR,SUNBURY TW16 7LN,MIDDX,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1993年 / 14期

关键词：

D O I：

10.1039/c39930001146

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Starting from D-(+)-galactose, the crystalline spirooxazolidin-2-one 2 can be readily prepared in an optically pure state by a nitrene-mediated four-step sequence, and serves to control both aldol and Diels-Alder reactions with high chiral efficiency, being easy to remove after use.

引用

页码：1146 / 1147

页数：2

共 10 条

[1] ENANTIOSPECIFIC PREPARATION OF [(2R, 6S)-ENDO]-5-AZA-1,10,10-TRIMETHYL-3-OXATRICYCLO[5.2.1.0(2,6)]DECAN-4-ONE BY A NITRENE-MEDIATED ROUTE FROM [(1S)-ENDO]-(-)-BORNEOL AND ITS UTILITY AS A CHIRAL AUXILIARY IN SOME ASYMMETRIC TRANSFORMATIONS
BANKS, MR
BLAKE, AJ
CADOGAN, JIG
DAWSON, IM
GOSNEY, I
GRANT, KJ
GAUR, S
HODGSON, PKG
KNIGHT, KS
SMITH, GW
STEVENSON, DE
[J]. TETRAHEDRON, 1992, 48 (37) : 7979 - 8006
[2] ASYMMETRIC ALDOL REACTIONS - A NEW CAMPHOR-DERIVED CHIRAL AUXILIARY GIVING HIGHLY STEREOSELECTIVE ALDOL REACTIONS OF BOTH LITHIUM AND TITANIUM(IV) ENOLATES
BONNER, MP
THORNTON, ER
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (04) : 1299 - 1308
[3] BIFUNCTIONAL CHIRAL AUXILIARIES .1. THE ALDOL REACTION BETWEEN DIALKYLBORON ENOLATES OF 1,3-DIPROPIONYL-TRANS-4,5-TETRAMETHYLENEIMIDAZOLIDIN-2-ONE AND ALDEHYDES
DAVIES, SG
MORTLOCK, AA
[J]. TETRAHEDRON LETTERS, 1991, 32 (36) : 4787 - 4790
[4] EINARSSON S, 1988, JANSEN CHIM ACTA, V6, P10
[5] Evans D. A., 1982, ALDRICHIM ACTA, V15, P23
[6] ASYMMETRIC DIELS-ALDER CYCLO-ADDITION REACTIONS WITH CHIRAL ALPHA, BETA-UNSATURATED N-ACYLOXAZOLIDINONES
EVANS, DA
CHAPMAN, KT
BISAHA, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) : 1238 - 1256
[7] ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES
EVANS, DA
BARTROLI, J
SHIH, TL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) : 2127 - 2129
[8] EVANS DA, 1984, ASYMMETRIC SYNTHESIS, V3, P1
[9] OPPOLZER W, 1990, J AM CHEM SOC, V112, P276
[10] ASYMMETRIC-SYNTHESIS OF (R)-(-)-MUSCONE AND (S)-(+)-MUSCONE BY ENANTIOSELECTIVE CONJUGATE ADDITION OF CHIRAL DIMETHYLCUPRATE TO (E)-CYCLOPENTADEC-2-EN-1-ONE
TANAKA, K
USHIO, H
KAWABATA, Y
SUZUKI, H
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (06): : 1445 - 1452

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