B-[3-((DIISOPROPYLAMINO)DIMETHYLSILYL)ALLYL]DIISOPINOCAMPHEYLBORANE - AN EXCELLENT REAGENT FOR THE STEREOSELECTIVE SYNTHESIS OF ANTI VICINAL DIOLS

被引：62

作者：

BARRETT, AGM

MALECHA, JW

机构：

[1] Department of Chemistry, Colorado State University, Fort Collins

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 18期

关键词：

D O I：

10.1021/jo00018a004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aldehydes reacted stereoselectively with B-[3-((diisopropylamino)dimethylsilyl)allyl]diisopinocampheylborane, derived from (+)- and (-)-alpha-pinene, to provide, on workup with hydrogen peroxide, (3S,4R)- and (3R,4S)-dihydroxy-1-alkenes, respectively.

引用

页码：5243 / 5245

页数：3

共 29 条

[1] THE TOTAL SYNTHESIS OF NIKKOMYCIN-B
BARRETT, AGM
LEBOLD, SA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (23) : 5818 - 5820
[2] CHIRAL SYNTHESIS VIA ORGANOBORANES .13. A HIGHLY DIASTEREOSELECTIVE AND ENANTIOSELECTIVE ADDITION OF [(Z)-GAMMA-ALKOXYALLYL]DIISOPINOCAMPHEYLBORANES TO ALDEHYDES
BROWN, HC
JADHAV, PK
BHAT, KS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) : 1535 - 1538
[3] CHIRAL SYNTHESIS VIA ORGANOBORANES .24. B-ALLYLBIS(2-ISOCARANYL)BORANE AS A SUPERIOR REAGENT FOR THE ASYMMETRIC ALLYLBORATION OF ALDEHYDES
BROWN, HC
RANDAD, RS
BHAT, KS
ZAIDLEWICZ, M
RACHERLA, US
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (06) : 2389 - 2392
[4] HYDROBORATION .61. DIISOPINOCAMPHEYLBORANE OF HIGH OPTICAL PURITY - IMPROVED PREPARATION AND ASYMMETRIC HYDROBORATION OF REPRESENTATIVE CIS-DISUBSTITUTED ALKENES
BROWN, HC
DESAI, MC
JADHAV, PK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (26) : 5065 - 5069
[5] CHIRAL SYNTHESIS VIA ORGANOBORANES .7. DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF ERYTHRO-BETA-METHYLOMOALLYL AND THREO-BETA-METHYLHOMOALLYL ALCHOLS VIA ENANTIOMERIC (Z)-CROTYLBORANE AND (E)-CROTYLBORANE
BROWN, HC
BHAT, KS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) : 5919 - 5923
[6] ASYMMETRIC CARBON CARBON BOND FORMATION VIA BETA-ALLYLDIISOPINOCAMPHEYLBORANE - SIMPLE SYNTHESIS OF SECONDARY HOMOALLYLIC ALCOHOLS WITH EXCELLENT ENANTIOMERIC PURITIES
BROWN, HC
JADHAV, PK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (07) : 2092 - 2093
[7] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES
DALE, JA
DULL, DL
MOSHER, HS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) : 2543 - &
[8] DANA G, 1967, B SOC CHIM FR, P3308
[9] METALATED ALLYLIC ETHERS AS HOMOENOLATE ANION EQUIVALENTS
EVANS, DA
ANDREWS, GC
BUCKWALT.B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (17) : 5560 - 5561
[10] FLEMING I, 1989, ORG REACTIONS, V37, P2

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