Selective reductions. 53. Asymmetric reduction of α-fluoromethyl ketones with B-chlorodiisopinocampheylborane and B-isopinocampheyl-9-borabicyclo [3.3. 1] …

PV Ramachandran, AV Teodorovic, B Gong…

Index: Ramachandran, P. Veeraraghavan; Teodorovic, Aleksandar V.; Gong, Baoqing; Brown, Herbert C. Tetrahedron: Asymmetry, 1994 , vol. 5, # 6 p. 1075 - 1086

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Citation Number: 48

Abstract

Abstract A systematic study of the asymmetric reduction of aryl and alkyl α-fluoroalkyl ketones with (−)-diisopinocampheylchloroborane ((−)-DIP-Chloride, 1), and (−)-B- isopinocampheyl-9-borabicyclo [3.3. 1] nonane (R-Alpine-Borane, 2) has been made. In the case of reagent 1, the direction of asymmetric induction in the chiral reduction of aryl trifluoromethyl ketones differs from that of the corresponding mono-and difluoromethyl ...