Tetrahedron Asymmetry p. 1929 - 1942 (1996)
Update date:2022-08-05
Topics:
Occhiato, Ernesto G.
Scarpi, Dina
Menchi, Gloria
Guarna, Antonio
The enantioselective reduction of γ-nitroketones 1-4 and γ-nitrodiketones 5-6 by the chiral reducing agent (+)- or (-)-diisopinocampheylchloroborane (DIP-Cl(TM)) afforded respectively nitroalcohols 7-9 with e.e's ranging from 33 to 86% and nitrodiols 11-12 with complete diastereoselectivity and e.e. > 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'-methoxyphenyl)-2,6-dioxaspiro[4.4]nonanes, 21 and 22, as EE/ZZ mixtures.
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Doi:10.1080/15257779508012536
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(1996)