Selective reductions. 52. Efficient asymmetric reduction of α-acetylenic α′-fluoroalkyl ketones with either B-chlorodiisopinocampheylborane or B-isopinocampheyl-9- …

PV Ramachandran, B Gong, AV Teodorovic…

Index: Ramachandran, P. Veeraraghavan; Gong, Baoqing; Teodorovic, Aleksandar V.; Brown, Herbert C. Tetrahedron: Asymmetry, 1994 , vol. 5, # 6 p. 1061 - 1074

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Citation Number: 46

Abstract

Abstract A systematic study of the asymmetric reduction of prochiral α-acetylenic α′- fluoroalkyl ketones with (−)-B-chlorodiisopinocampheylborane [(−)-DIP-Chloride, 1] and (−)- B-isopinocampheyl-9-borabicyclo [3.3. 1] nonane (R-Alpine-Borane, 2) reveals that perfluoroalkyl acetylenic ketones can be reduced in very high ee (92->-99%) with both of these reagents. For example, 1, 1, 1-trifluoro-4-phenyl-3-butyn-2-one, 1, 1, 1, 2, 2- ...