A dynamic kinetic esolution of allyl alcohols by the combined use of lipases and [VO(OSiPh3)3]

被引:112
作者
Akai, S
Tanimoto, K
Kanao, Y
Egi, M
Yanamoto, T
Kita, Y
机构
[1] Univ Shizuoka, Sch Pharmaceut Sci, Suruga Ku, Shizuoka 4228526, Japan
[2] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan
关键词
allyl alcohols; asymmetric synthesis; dynamic kinetic resolution; lipases; vanadium;
D O I
10.1002/anie.200503765
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Mix and match: A new type of dynamic kinetic resolution of racemic allyl alcohols uses a combination of lipases and [VO(OSiPh3)3] (1). The 1,3-transposition of allyl alcohols catalyzed by 1 gave thermodynamic mixtures of two regioisomers, which underwent highly enantio-and chemoselective esterification with lipases. Optically enriched allyl acetates were isolated in high yields. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2592 / 2595
页数:4
相关论文
共 48 条
[11]   Catalytic racemisation of alcohols: Applications to enzymatic resolution reactions [J].
Dinh, PM ;
Howarth, JA ;
Hudnott, AR ;
Williams, JMJ ;
Harris, W .
TETRAHEDRON LETTERS, 1996, 37 (42) :7623-7626
[12]   One-pot synthesis of enantiopure syn-1,3-diacetates from racemic syn/anti mixtures of 1,3-diols by dynamic kinetic asymmetric transformation [J].
Edin, M ;
Steinreiber, J ;
Bäckvall, JE .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (16) :5761-5766
[13]   Mechanism of enantioselectivity of lipases and other synthetically useful hydrolases [J].
Ema, T .
CURRENT ORGANIC CHEMISTRY, 2004, 8 (11) :1009-1025
[14]   STEREOSPECIFIC SYNTHESES AND REACTIONS OF ALLYL-SILANE AND ALLENYL-SILANE [J].
FLEMING, I ;
TERRETT, NK .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1984, 264 (1-2) :99-118
[15]   Kinetic resolution of racemic cyclic olefins via chiral dioxirane [J].
Frohn, M ;
Zhou, XM ;
Zhang, JR ;
Tang, Y ;
Shi, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (33) :7718-7719
[16]   Palladium-catalyzed asymmetric synthesis of allylic alcohols from unsymmetrical and symmetrical racemic allylic carbonates featuring C-O-bond formation and dynamic kinetic resolution [J].
Gais, HJ ;
Bondarev, O ;
Hetzer, R .
TETRAHEDRON LETTERS, 2005, 46 (37) :6279-6283
[17]   Enantioselective enzymatic desymmetrizations in organic synthesis [J].
García-Urdiales, E ;
Alfonso, I ;
Gotor, V .
CHEMICAL REVIEWS, 2005, 105 (01) :313-354
[18]   Application of lipases in kinetic resolution of racemates [J].
Ghanem, A ;
Aboul-Enein, HY .
CHIRALITY, 2005, 17 (01) :1-15
[19]  
GRANCHELLI FE, 1958, Patent No. 2863891
[20]  
Hanson, 2002, ORG REACTIONS, V60, P1