The kinetic resolution of allylic alcohols by a non-enzymatic acylation catalyst; application to natural product synthesis

被引:107
作者
Bellemin-Laponnaz, S [1 ]
Tweddell, J [1 ]
Ruble, JC [1 ]
Breitling, FM [1 ]
Fu, GC [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
D O I
10.1039/b002041i
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A planar-chiral DMAP derivative is shown to serve as an effective catalyst for the kinetic resolution of allylic alcohols; to illustrate its practical utility, the catalyst is applied to the resolution of two alcohols that have been employed as intermediates in recent natural product total syntheses.
引用
收藏
页码:1009 / 1010
页数:2
相关论文
共 22 条
[1]  
BORMAN S, 1998, CHEM ENG NEWS 1214, P15
[2]  
BORMAN S, 2000, CHEM ENG NEWS 0131, P7
[3]   Enantioselective synthesis of beta-substituted butyric acid derivatives via orthoester Claisen rearrangement of enzymatically resolved allylic alcohols: application to the synthesis of (R)-(-)-baclofen [J].
Brenna, E ;
Caraccia, N ;
Fuganti, C ;
Fuganti, D ;
Grasselli, P .
TETRAHEDRON-ASYMMETRY, 1997, 8 (22) :3801-3805
[4]   Minimal acylase-like peptides. Conformational control of absolute stereospecificity [J].
Copeland, GT ;
Jarvo, ER ;
Miller, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (20) :6784-6785
[5]  
Drauz K., 1995, ENZYME CATALYSIS ORG
[6]   STUDIES DIRECTED TOWARD THE DESIGN OF CHIRAL ACYLATING AGENTS - THE UTILITY OF CHIRAL N-BENZOYLIMIDES IN ENANTIOSELECTIVE ALCOHOL ACYLATION [J].
EVANS, DA ;
ANDERSON, JC ;
TAYLOR, MK .
TETRAHEDRON LETTERS, 1993, 34 (35) :5563-5566
[7]   Nucleophilic catalysis with π-bound nitrogen heterocycles:: Synthesis of the first ruthenium catalysts and comparison of the reactivity and the enantioselectivity of ruthenium and iron complexes [J].
Garrett, CE ;
Fu, GC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (30) :7479-7483
[8]   A biomimetic approach to asymmetric acyl transfer catalysis [J].
Jarvo, ER ;
Copeland, GT ;
Papaioannou, N ;
Bonitatebus, PJ ;
Miller, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (50) :11638-11643
[9]  
Johnson R.A., 1991, Comprehensive Organic Synthesis, V7
[10]  
Kagan H.B., 2007, TOPICS STEREOCHEMIST, V18, P249, DOI 10.1002/9780470147276.ch4