New and improved ligands for highly enantioselective catalytic diphenylzinc additions to aryl aldehydes

被引：86

作者：

Huang, WS ^{[1
]}

Pu, L ^{[1
]}

机构：

[1] Univ Virginia, Dept Chem, Charlottesville, VA 22901 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 02期

关键词：

D O I：

10.1016/S0040-4039(99)02041-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

By introducing electron-withdrawing fluorine atoms to a chiral 1,1'-binaphthyl ligand (R)-1, a new catalyst (S)-5d has been obtained which shows improved catalytic properties for the asymmetric diphenylzinc addition to aldehydes. This new ligand allows the synthesis of chiral diarylcarbinols with high enantioselectivity in shorter reaction time under simple reaction conditions. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：145 / 149

页数：5

共 29 条

[1] Catalytic enantioselective aryl transfer:: asymmetric addition of diphenylzinc to aldehydes
Bolm, C
Muñiz, K
[J]. CHEMICAL COMMUNICATIONS, 1999, (14) : 1295 - 1296
[2] Synthesis of aryl 2-benzofuranyl and aryl 2-indolyl carbinols of high enantiomeric purity via palladium-catalyzed heteroannulation of chiral arylpropargylic alcohols
Botta, M
Summa, V
Corelli, F
DiPietro, G
Lombardi, P
[J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (05) : 1263 - 1266
[3] PREPARATIVE SYNTHESES OF OPTICALLY PURE ORTHOSUBSTITUTED BENZHYDROLS BY ASYMMETRIC REDUCTIONS OF THE CORRESPONDING BENZOPHENONES
BROWN, E
LEZE, A
TOUET, J
[J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (07) : 841 - 844
[4] Asymmetric synthesis of (S)-carbinoxamine. New aspects of oxazaborolidine-catalyzed enantioselective carbonyl reduction
Corey, EJ
Helal, CJ
[J]. TETRAHEDRON LETTERS, 1996, 37 (32) : 5675 - 5678
[5] Catalytic enantioselective synthesis of the second generation histamine antagonist cetirizine hydrochloride
Corey, EJ
Helal, CJ
[J]. TETRAHEDRON LETTERS, 1996, 37 (28) : 4837 - 4840
[6] NOVEL ELECTRONIC EFFECTS OF REMOTE SUBSTITUENTS ON THE OXAZABOROLIDINE-CATALYZED ENANTIOSELECTIVE REDUCTION OF KETONES
COREY, EJ
HELAL, CJ
[J]. TETRAHEDRON LETTERS, 1995, 36 (50) : 9153 - 9156
[7] Planar-chiral heterocycles as ligands in metal-catalyzed processes: Enantioselective addition of organozinc reagents to aldehydes
Dosa, PI
Ruble, JC
Fu, GC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (03) : 444 - 445
[8] HU QS, UNPUB
[9] The first highly enantioselective catalytic diphenylzinc additions to aldehydes: Synthesis of chiral diarylcarbinols by asymmetric catalysis
Huang, WS
Pu, L
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12) : 4222 - 4223
[10] From highly enantioselective monomeric catalysts to highly enantioselective polymeric catalysts: Application of rigid and sterically regular chiral binaphthyl polymers to the asymmetric synthesis of chiral secondary alcohols
Huang, WS
Hu, QS
Pu, L
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (21) : 7940 - 7956

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