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, A.r., 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
BOTTA, MAURIZIO;TAFI, ANDREA
1992-01-01
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.
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https://hdl.handle.net/11365/33941
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