Toward a versatile allylation reagent: Practical, enantioselective allylation of acylhydrazones using strained silacycles

被引:102
作者
Berger, R [1 ]
Rabbat, PMA [1 ]
Leighton, JL [1 ]
机构
[1] Columbia Univ, Dept Chem, New York, NY 10027 USA
关键词
D O I
10.1021/ja035001g
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 acylhydrazones has been developed. The previously reported strained silacycle reagent 1 reacts with a wide variety of acylhydrazones to give the hydrazide products with good enantioselectivity (83-89% ee, typically). It has been demonstrated that the products may be isolated without chromatography by recrystallization in ≥98% ee. Copyright © 2003 American Chemical Society.
引用
收藏
页码:9596 / 9597
页数:2
相关论文
共 30 条
[11]   Enantioselective synthesis of homoallylamines by nucleophilic addition of chirally modified allylboron reagents to imines [J].
Itsuno, S ;
Watanabe, K ;
Ito, K ;
ElShehawy, AA ;
Sarhan, AA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (1-2) :109-110
[12]  
Itsuno S, 1999, SYNLETT, P1987
[13]   Enantioselective synthesis of optically active homoallylamines by nucleophilic addition of chirally modified allylboranes to N-silylimines [J].
Itsuno, S ;
Watanabe, K ;
Matsumoto, T ;
Kuroda, S ;
Yokoi, A ;
El-Shehawy, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (14) :2011-2016
[14]   Strained silacycles in organic synthesis: A new reagent for the enantioselective allylation of aldehydes [J].
Kinnaird, JWA ;
Ng, PY ;
Kubota, K ;
Wang, XL ;
Leighton, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (27) :7920-7921
[15]   STEREOSELECTIVE ALLYLATION OF BETA-HYDROXY-ALPHA,BETA-ENONES AND BETA-AMINO-ALPHA,BETA-ENONES WITH ALLYLTRIFLUOROSILANE TRIETHYLAMINE SYSTEMS [J].
KIRA, M ;
SATO, K ;
SEKIMOTO, K ;
GEWALD, R ;
SAKURAI, H .
CHEMISTRY LETTERS, 1995, (04) :281-282
[16]   Catalytic enantioselective addition to imines [J].
Kobayashi, S ;
Ishitani, H .
CHEMICAL REVIEWS, 1999, 99 (05) :1069-1094
[17]   Highly stereoselective synthesis of homoallylic amines based on addition of allyltrichlorosilanes to benzoylhydrazones under neutral conditions [J].
Kobayashi, S ;
Hirabayashi, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (29) :6942-6943
[18]   A highly practical and enantioselective reagent for the allylation of aldehydes [J].
Kubota, K ;
Leighton, JL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (08) :946-+
[19]  
Marshall JA, 2000, ANGEW CHEM INT EDIT, V39, P953, DOI 10.1002/(SICI)1521-3773(20000303)39:5<953::AID-ANIE953>3.0.CO
[20]  
2-I