Enantioselective allylation of ketone-derived benzoylhydrazones: Practical synthesis of tertiary carbinarnines

被引：113

作者：

Berger, R ^{[1
]}

Duff, K ^{[1
]}

Leighton, JL ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 18期

关键词：

D O I：

10.1021/ja0486418

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly practical method for the enantioselective allylation of ketone-derived benzoylhydrazones has been developed. The previously reported strained silacycle reagent 1 reacts with a wide variety of benzoylhydrazones to give the hydrazide products with good to excellent enantioselectivity (84-97% ee). A mechanism in which the acylhydrazone becomes caovalently attached to the silane has been established. Copyright © 2003 American Chemical Society.

引用

页码：5686 / 5687

页数：2

共 19 条

[11] Comparison of phosphorus and silicon: Hypervalency, stereochemistry, and reactivity
Holmes, RR
[J]. CHEMICAL REVIEWS, 1996, 96 (03) : 927 - 950
[12] STEREOSELECTIVE ADDITION-REACTIONS OF CHIRAL N-BENZYLIDENE-PARA-TOLUENESULFINAMIDES - ASYMMETRIC SYNTHESES OF BETA-AMINO AND GAMMA-AMINO ACIDS
HUA, DH
MIAO, SW
CHEN, JS
IGUCHI, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) : 4 - 6
[13] Chiral Sulfoxides as neutral coordinate-organocatalysts in asymmetric allylation of N-acylhydrazones using allyltrichlorosilanes
Kobayashi, S
Ogawa, C
Konishi, H
Sugiura, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (22) : 6610 - 6611
[14] LEIGHTON JL, UNPUB
[15] Stereoselective synthesis of both syn- and anti-n-tert-alkylamines using highly stereospecific crotylation of ketone-derived acylhydrazones with crotyltrichlorosilanes
Ogawa, C
Sugiura, M
Kobayashi, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (15) : 5359 - 5364
[16] Triflimide activation of a chiral oxazaborolidine leads to a more general catalytic system for enantioselective Diels-Alder addition
Ryu, DH
Corey, EJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (21) : 6388 - 6390
[17] Broad-spectrum enantioselective Diels-Alder catalysis by chiral, cationic oxazaborolidines
Ryu, DH
Lee, TW
Corey, EJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (34) : 9992 - 9993
[18] The first catalytic highly enantioselective alkylation of ketimines -: A novel approach to optically active quaternary α-amino acids
Saaby, S
Nakama, K
Lie, MA
Hazell, RG
Jorgensen, KA
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (24) : 6145 - 6154
[19] Amines via nucleophilic 1,2-addition to ketimines.: Construction of nitrogen-substituted quaternary carbon atoms.: A review
Steinig, AG
Spero, DM
[J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2000, 32 (03) : 205 - +

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