Synthesis of enantiopure 2, 7-diaryl-1, 6-dioxaspiro [4.4] nonanes via enantioselective reduction of prochiral γ-nitroketones by diisopinocampheylchloroborane (DIP- …

EG Occhiato, D Scarpi, G Menchi, A Guarna

Index: Occhiato, Ernesto G.; Scarpi, Dina; Menchi, Gloria; Guarna, Antonio Tetrahedron Asymmetry, 1996 , vol. 7, # 7 p. 1929 - 1942

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Citation Number: 11

Abstract

The enantioselective reduction of γ-nitroketones 1–4 and γ-nitrodiketones 5–6 by the chiral reducing agent (+)-or (−)-diisopinocampheylchloroborane (DIP-C1™) afforded respectively nitroalcohols 7–9 with ee's ranging from 33 to 86% and nitrodiols 11–12 with complete diastereoselectivity and ee> 95%. Nitrodiols (1S, 7S)-11 and (1S, 7S)-12 were then used as chiral precursors for the synthesis of the enantiopure 2, 7-diphenyl-and 2, 7-di-(2′- ...