A mild, enantioselective synthesis of (R)-salmeterol via sodium borohydride-calcium chloride asymmetric reduction of a phenacyl phenylglycinol derivative

被引:24
作者
Bream, RN
Ley, SV
McDermott, B
Procopiou, PA
机构
[1] GlaxoSmithKline Med Res Ctr, Stevenage SG1 2NY, Herts, England
[2] Univ Cambridge, Chem Lab, Cambridge CB2 1EW, England
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2002年 / 20期
关键词
D O I
10.1039/b207068p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A short and efficient enantioselective route to (R)- salmeterol involving asymmetric reduction of a phenylglycinyl ketone derivative followed by reductive amination of the resulting amino alcohol and hydrogenolysis is described.
引用
收藏
页码:2237 / 2242
页数:6
相关论文
共 14 条
[1]   REDUCTIVE AMINATION OF ALDEHYDES AND KETONES BY USING SODIUM TRIACETOXYBOROHYDRIDE [J].
ABDELMAGID, AF ;
MARYANOFF, CA ;
CARSON, KG .
TETRAHEDRON LETTERS, 1990, 31 (39) :5595-5598
[2]  
BREAM RN, IN PRESS ORG LETT
[3]  
Evans B., 1991, EP-A, Patent No. 422889
[4]   A PRACTICAL AND STEREOSELECTIVE REDUCTION OF 3-KETO-2-METHYL ESTERS OR 3-KETO-2-METHYL AMIDES INTO ERYTHRO-3-HYDROXY-2-METHYL ESTERS OR ERYTHRO-3-HYDROXY-2-METHYL AMIDES WITH NABH4 CATALYZED BY MNCL2 [J].
FUJII, H ;
OSHIMA, K ;
UTIMOTO, K .
TETRAHEDRON LETTERS, 1991, 32 (43) :6147-6150
[5]   ENANTIOSELECTIVE SYNTHESIS OF SALMETEROL VIA ASYMMETRIC BORANE REDUCTION [J].
HETT, R ;
STARE, R ;
HELQUIST, P .
TETRAHEDRON LETTERS, 1994, 35 (50) :9375-9378
[6]  
Judkins B. D., 1991, Eur. Patent Appl., Patent No. 460924
[7]   A NEW AND SELECTIVE METHOD OF OXIDATION - THE CONVERSION OF ALKYL HALIDES AND ALKYL TOSYLATES TO ALDEHYDES [J].
KORNBLUM, N ;
JONES, WJ ;
ANDERSON, GJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (15) :4113-4114
[8]  
NAILS AT, 1994, J AM REV RESP DIS, V149, pA481
[9]   STEREOSELECTIVE REDUCTION OF BETA-KETO-ESTERS WITH ZINC BOROHYDRIDE - STEREOSELECTIVE SYNTHESIS OF ERYTHRO-3-HYDROXY-2-ALKYLPROPIONATES [J].
NAKATA, T ;
OISHI, T .
TETRAHEDRON LETTERS, 1980, 21 (17) :1641-1644
[10]   Enantioselective synthesis of (S)-salmeterol via asymmetric reduction of azidoketone by Pichia angusta [J].
Procopiou, PA ;
Morton, GE ;
Todd, M ;
Webb, G .
TETRAHEDRON-ASYMMETRY, 2001, 12 (14) :2005-2008