A highly practical and enantioselective reagent for the allylation of aldehydes

被引：130

作者：

Kubota, K ^{[1
]}

Leighton, JL ^{[1
]}

机构：

[1] Columbia Univ, Dept Chem, New York, NY 10027 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 08期

关键词：

D O I：

10.1002/anie.200390252

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Strain at silicon is the key to success of reagent 1 since this strain, which is induced by the diazasilacyclopentane ring, determines its reactivity. This practical and general new reagent for the highly enantioselective allylation of aldehydes is easily prepared as an air-stable solid and may be stored without significant decomposition.

引用

页码：946 / +

页数：4

共 27 条

[1] [Anonymous], MODERN CARBONYL CHEM
[2] 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
[3] A PRACTICAL AND EFFICIENT METHOD FOR ENANTIOSELECTIVE ALLYLATION OF ALDEHYDES
COREY, EJ
YU, CM
KIM, SS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) : 5495 - 5496
[4] Denmark S. E., 2000, MODERN CARBONYL CHEM
[5] ASYMMETRIC ALLYLATION OF ALDEHYDES WITH CHIRAL LEWIS-BASES
DENMARK, SE
COE, DM
PRATT, NE
GRIEDEL, BD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) : 6161 - 6163
[6] Catalytic, enantioselective addition of substituted allylic trichlorosilanes using a rationally-designed 2,2′-bispyrrolidine-based bisphosphoramide
Denmark, SE
Fu, JP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (38) : 9488 - 9489
[7] On the mechanism of catalytic, enantioselective allylation of aldehydes with chlorosilanes and chiral Lewis bases
Denmark, SE
Fu, JP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (48) : 12021 - 12022
[8] A stereochemical model for merged 1,2- and 1,3-asymmetric induction in diastereoselective Mukaiyama aldol addition reactions and related processes
Evans, DA
Dart, MJ
Duffy, JL
Yang, MG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (18) : 4322 - 4343
[9] ENANTIOSELECTIVE SYNTHESES OF SECONDARY HOMOALLYL ALCOHOLS WITH OPTICALLY-ACTIVE ETA-3-ALLYLMOLYBDENUM COMPLEXES
FALLER, JW
LINEBARRIER, DL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (05) : 1937 - 1939
[10] ENANTIOSELECTIVE ALLYLTITANATION OF ALDEHYDES WITH CYCLOPENTADIENYLDIALKOXYALLYLTITANIUM COMPLEXES
HAFNER, A
DUTHALER, RO
MARTI, R
RIHS, G
ROTHESTREIT, P
SCHWARZENBACH, F
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (07) : 2321 - 2336

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