Molecular mechanics calculations for the 1-substituted bicyclo[3.3.1]nonan-2-ones 2a-d show that the amount of the chair-boat conformation increases as the size of the substituent at C1 increases. This result sharply fits with the stereochemical course of NaBH4 reductions of ketones 2a-d if axial attack on the chair-boat conformation and equatorial attack on the chair-chair one are assumed to be preferential.

GAMBACORTA A, DELLOJACONO AR, BOTTA M, & TAFI A (1992). CONFORMATIONAL EFFECTS ON THE STEREOCHEMICAL COURSE OF THE NABH4 REDUCTION OF SUBSTITUTED BICYCLO[3.3.1]NONAN-2-ONES. GAZZETTA CHIMICA ITALIANA, 122(9), 355-359.

CONFORMATIONAL EFFECTS ON THE STEREOCHEMICAL COURSE OF THE NABH4 REDUCTION OF SUBSTITUTED BICYCLO[3.3.1]NONAN-2-ONES

GAMBACORTA, Augusto;
1992

Abstract

Molecular mechanics calculations for the 1-substituted bicyclo[3.3.1]nonan-2-ones 2a-d show that the amount of the chair-boat conformation increases as the size of the substituent at C1 increases. This result sharply fits with the stereochemical course of NaBH4 reductions of ketones 2a-d if axial attack on the chair-boat conformation and equatorial attack on the chair-chair one are assumed to be preferential.
GAMBACORTA A, DELLOJACONO AR, BOTTA M, & TAFI A (1992). CONFORMATIONAL EFFECTS ON THE STEREOCHEMICAL COURSE OF THE NABH4 REDUCTION OF SUBSTITUTED BICYCLO[3.3.1]NONAN-2-ONES. GAZZETTA CHIMICA ITALIANA, 122(9), 355-359.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11590/143921
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