Synthetic applicability and in situ recycling of a B-methoxy oxazaborolidne catalyst derived from cis-1-amino-indan-2-ol

被引:27
作者
Gilmore, NJ [1 ]
Jones, S [1 ]
Muldowney, MP [1 ]
机构
[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England
关键词
D O I
10.1021/ol048916o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A procedure is described that greatly simplifies the use of an oxazaborolidine catalyst derived from (1R,2S) cis-1-amino-indan-2-ol. This B-OMe catalyst has been employed in the asymmetric reduction of a number of structurally diverse prochiral ketones, in particular the reduction of alpha-amino acetophenone and its derivatives. A method for reducing the effective catalyst loading by "in situ recycling" is also presented.
引用
收藏
页码:2805 / 2808
页数:4
相关论文
共 26 条
[1]  
Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P1987, DOI 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO
[2]  
2-Z
[3]   HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].
COREY, EJ ;
BAKSHI, RK ;
SHIBATA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553
[4]   CHEMOENZYMATIC SYNTHESIS OF 1,2-AMINO-ALCOHOLS AND 1,3-AMINO-ALCOHOLS AND THEIR USE IN THE ENANTIOSELECTIVE REDUCTION OF ACETOPHENONE AND ANTI-ACETOPHENONE OXIME METHYL-ETHER WITH BORANE [J].
DIDIER, E ;
LOUBINOUX, B ;
TOMBO, GMR ;
RIHS, G .
TETRAHEDRON, 1991, 47 (27) :4941-4958
[5]  
DISIMONE B, 1995, TETRAHEDRON-ASYMMETR, V6, P301
[6]   Efficient desymmetrisation of a meso-imide using a chiral oxazaborolidine catalyst [J].
Dixon, RA ;
Jones, S .
TETRAHEDRON-ASYMMETRY, 2002, 13 (10) :1115-1119
[7]   A scalable asymmetric synthesis of (R)-2-amino-1-(3-pyridinyl)ethanol dihydrochloride via an oxazaborolidine catalyzed borane reduction [J].
Duquette, J ;
Zhang, MB ;
Zhu, L ;
Reeves, RS .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2003, 7 (03) :285-288
[8]   Evaluating the role of solvent and borane on the enantioselectivity of the oxazaborolidine reduction of prochiral ketones using catalysts derived from cis-(1R,2S)-1-amino-indan-2-ol [J].
Gilmore, NJ ;
Jones, S .
TETRAHEDRON-ASYMMETRY, 2003, 14 (15) :2115-2118
[9]   Large-scale synthesis of enantio- and diastereomerically pure (R,R)-formoterol [J].
Hett, R ;
Fang, QK ;
Gao, Y ;
Wald, SA ;
Senanayake, CH .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 1998, 2 (02) :96-99
[10]   Enantio- and diastereoselective synthesis of all four stereoisomers of formoterol [J].
Hett, R ;
Fang, QK ;
Gao, Y ;
Hong, YP ;
Butler, HT ;
Nie, XY ;
Wald, SA .
TETRAHEDRON LETTERS, 1997, 38 (07) :1125-1128