The dual-catalyzed (amino alcohol Lewis acid) enantioselective addition of diethylzinc to N-diphenylphosphinoyl imines

被引：40

作者：

Jimeno, C ^{[1
]}

Vidal-Ferran, A ^{[1
]}

Moyano, A ^{[1
]}

Pericàs, MA ^{[1
]}

Riera, A ^{[1
]}

机构：

[1] Univ Barcelona, Dept Quim Organ, Unitat Reccerca Sintesi Aismetr, E-08028 Barcelona, Spain

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 04期

关键词：

imines; addition reactions; zinc and compounds; asymmetric induction;

D O I：

10.1016/S0040-4039(98)02410-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optimal structural characteristics within a family of (2R,3R)-1-alkoxy-3-dialkylamino-3-phenyl-2-propanols have been determined for maximum enantioselectivity in the addition of diethylzinc to N-diphenylphosphinoyl imines (1-alkoxy = trityloxy; 3-dialkylamino = piperidino). The simultaneous use of silylating agents acting as Lewis acids to induce rate acceleration has been investigated, allowing the identification of triisopropylsilyl chloride and tert-butyldiphenylsilyl chloride as the most efficient mediators in terms of rate enhancement and enantiomeric excess of the resulting phosphinamides. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：777 / 780

页数：4

共 50 条

[21] Syntheses and crystal structures of chiral BINOL derivatives and their applications in enantioselective lewis acid catalyzed addition of diethylzinc to aldehydes
Liu Guo-Hua
Yu Han
Yang Liang-Zhun
Yao Mei
Fang Hai-Bin
Xue Yun-Ning
CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2007, 26 (04) : 477 - 483
[22] Syntheses and Crystal Structures of Chiral BINOL Derivatives and Their Applications in Enantioselective Lewis Acid Catalyzed Addition of Diethylzinc to Aldehydes
刘国华
余焓
姚美
方海斌
薛允宁
Chinese Journal of Structural Chemistry, 2007, (04) : 477 - 483
[23] Syntheses and Crystal Structures of Chiral BINOL Derivatives and Their Applications in Enantioselective Lewis Acid Catalyzed Addition of Diethylzinc to Aldehydes
刘国华
余焓
姚美
方海斌
薛允宁
结构化学, 2007, (04) : 477 - 483
[24] Enantioselective addition of diethylzinc to aryl aldehydes catalyzed by 1,2,3,4-tetrahydroisoquinoline β-amino alcohol
Geng Xu
Chinese Chemical Letters, 2010, 21 (03) : 309 - 311
[25] Enantioselective addition of diethylzinc to aryl aldehydes catalyzed by 1,2,3,4-tetrahydroisoquinoline β-amino alcohol
Xu, Geng
Liu, Zhan Zhu
CHINESE CHEMICAL LETTERS, 2010, 21 (03) : 309 - 311
[26] Enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl) imines promoted by 2-azanorbornylmethanols
Guijarro, D
Pinho, P
Andersson, PG
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08): : 2530 - 2535
[27] Enantioselective addition of diethylzinc to aldehydes catalyzed by a new chiral β-amino alcohol derived from D-mannitol
Cho, BT
Chun, YS
TETRAHEDRON-ASYMMETRY, 1998, 9 (09) : 1489 - 1492
[28] Highly enantioselective addition of diethylzinc to aldehydes catalyzed by isoindolinyl alcohol as a chiral ligand
Park, DH
Choi, HJ
Lee, S
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2003, 24 (11) : 1559 - 1560
[29] Enantioselective addition of diethylzinc to aldehydes catalyzed by γ-amino alcohols derived from (+)- and (-)-α-pinene
Szakonyi, Z
Balázs, A
Martinek, TA
Fülöp, F
TETRAHEDRON-ASYMMETRY, 2006, 17 (02) : 199 - 204
[30] Enantioselective Addition of Diethylzinc to Aromatic Aldehydes Catalyzed by Pyrolidine and Piperidine -Amino Alcohols
Salehi, Peyman
Dabiri, Minoo
Kozehgary, Gholamreza
Heydari, Seddigheh
SYNTHETIC COMMUNICATIONS, 2009, 39 (14) : 2575 - 2584

← 1 2 3 4 5 →