EFFICIENT ASYMMETRIC-SYNTHESIS OF ANTI-ALDOLS FROM BORNANESULTAM DERIVED BORYL ENOLATES

被引：67

作者：

OPPOLZER, W

LIENARD, P

机构：

[1] Département de Chimie Organique, Université de Genève

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 27期

关键词：

D O I：

10.1016/S0040-4039(00)79339-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

O-Borylation of N-propionylsultam 1 provides in situ boryl enolate 6 which, at -78-degrees-C in the presence of TiCl4, reacts with aliphatic, aromatic and alpha, beta-unsaturated aldehydes giving mostly crystalline, diastereomerically pure anti-aldols 3.

引用

页码：4321 / 4324

页数：4

共 7 条

[1] STEREOSELECTIVE ALDOL REACTIONS OF CHLOROTITANIUM ENOLATES - AN EFFICIENT METHOD FOR THE ASSEMBLAGE OF POLYPROPIONATE-RELATED SYNTHONS
EVANS, DA
RIEGER, DL
BILODEAU, MT
URPI, F
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) : 1047 - 1049
[2] ENANTIOMERICALLY PURE, CRYSTALLINE ANTI-ALDOLS FROM N-ACYLBORNANESULTAMS - ALDOLIZATION AND STRUCTURE OF INTERMEDIATE TERT-BUTYLDIMETHYLSILYL-N,O-KETENE ACETAL
OPPOLZER, W
STARKEMANN, C
RODRIGUEZ, I
BERNARDINELLI, G
[J]. TETRAHEDRON LETTERS, 1991, 32 (01) : 61 - 64
[3] BORNANESULTAM-DIRECTED ASYMMETRIC-SYNTHESIS OF CRYSTALLINE, ENANTIOMERICALLY PURE SYN ALDOLS
OPPOLZER, W
BLAGG, J
RODRIGUEZ, I
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[4] STEREOCONTROLLED SYNTHESES OF POLYSUBSTITUTED 2,3-DIHYDRO-4H-PYRAN-4-ONES BY CYCLOCONDENSATION OF BETA-ACYLOXY-KETONES
OPPOLZER, W
RODRIGUEZ, I
[J]. HELVETICA CHIMICA ACTA, 1993, 76 (03) : 1282 - 1291
[5] NONDESTRUCTIVE CLEAVAGE OF N-ACYLSULTAMS UNDER NEUTRAL CONDITIONS - PREPARATION OF ENANTIOMERICALLY, PURE FMOC-PROTECTED ALPHA-AMINO-ACIDS
OPPOLZER, W
LIENARD, P
[J]. HELVETICA CHIMICA ACTA, 1992, 75 (08) : 2572 - 2582
[6] POPPOLZER W, 1993, HELV CHIM ACTA, V76, P1275
[7] ACYCLIC STEREOSELECTION .54. EXTENDING THE SCOPE OF THE EVANS ASYMMETRIC ALDOL REACTION - PREPARATION OF ANTI-ALDOLS AND NON-EVANS SYN-ALDOLS
WALKER, MA
HEATHCOCK, CH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) : 5747 - 5750

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