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Chiral synthesis via organoboranes. 41. The utility of B ‐chlorodiisopinocampheylborane for a general synthesis of enantiomerically pure drugs
Author(s) -
Ramachandran P. Veeraraghavan,
Gong Baoqing,
Brown Herbert C.
Publication year - 1995
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530070209
Subject(s) - chemistry , piperazine , stereochemistry , enantioselective synthesis , enantiomer , catalysis , organic chemistry
Abstract A general approach to the synthesis of enantiomerically pure α‐phenyl amino alcohols via the asymmetric reduction of α‐phenyl haloalkyl ketones or α‐phenyl aminoalkyl ketones with B ‐chlorodiisopinocampheylborane is described. Using this approach, an improved synthesis of a potential antipsychotic, α‐(4‐fluorophenyl)‐4‐(2‐pyrimidinyl)‐1‐piperazinebutanol in ⩾98% ee, and the broncholdilator 1‐(2‐methoxy‐2‐phenethyl)‐4‐(3‐hydroxy‐3‐phenylpropyl)piperazine (eprozinol) in ⩾99% ee is achieved. © 1995 Wiley‐Liss, Inc.