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Chiral synthesis via organoboranes. 41. The utility of B-chlorodiisopinocampheylborane for a general synthesis of enantiomerically pure drugs
P. Veeraraghavan Ramachandran,
Baoqing Gong,
Herbert C. Brown,
Corresponding Author
P. Veeraraghavan Ramachandran
Herbert C. Brown and R. B. Wetherill Laboratories of Chemistry, Purdue University, West Lafayette, Indiana
H.C. Brown and R.B. Wetherill Laboratories of Chemistry, Purdue University, West Lafayett, IN 47907Search for more papers by this authorBaoqing Gong
Herbert C. Brown and R. B. Wetherill Laboratories of Chemistry, Purdue University, West Lafayette, Indiana
Search for more papers by this authorCorresponding Author
Herbert C. Brown
Herbert C. Brown and R. B. Wetherill Laboratories of Chemistry, Purdue University, West Lafayette, Indiana
H.C. Brown and R.B. Wetherill Laboratories of Chemistry, Purdue University, West Lafayett, IN 47907Search for more papers by this authorP. Veeraraghavan Ramachandran,
Baoqing Gong,
Herbert C. Brown,
Corresponding Author
P. Veeraraghavan Ramachandran
Herbert C. Brown and R. B. Wetherill Laboratories of Chemistry, Purdue University, West Lafayette, Indiana
H.C. Brown and R.B. Wetherill Laboratories of Chemistry, Purdue University, West Lafayett, IN 47907Search for more papers by this authorBaoqing Gong
Herbert C. Brown and R. B. Wetherill Laboratories of Chemistry, Purdue University, West Lafayette, Indiana
Search for more papers by this authorCorresponding Author
Herbert C. Brown
Herbert C. Brown and R. B. Wetherill Laboratories of Chemistry, Purdue University, West Lafayette, Indiana
H.C. Brown and R.B. Wetherill Laboratories of Chemistry, Purdue University, West Lafayett, IN 47907Search for more papers by this authorAbstract
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.
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