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. 2009 Dec 11;20(23):2659-2665.
doi: 10.1016/j.tetasy.2009.11.009.

Chiral spiroaminoborate ester as a highly enantioselective and efficient catalyst for the borane reduction of furyl, thiophene, chroman and thiochroman containing ketones

Viatcheslav Stepanenko  1 , Melvin De Jesús, Wildeliz Correa, Lorianne Bermúdez, Cindybeth Vázquez, Irisbel Guzmán, Margarita Ortiz-Marciales
Affiliations

Chiral spiroaminoborate ester as a highly enantioselective and efficient catalyst for the borane reduction of furyl, thiophene, chroman and thiochroman containing ketones

Viatcheslav Stepanenko et al. Tetrahedron Asymmetry. .

Abstract

Prochiral heteroaryl ketones containing furan, thiophene, chroman and thiochroman moieties were successfully reduced in the presence of 1 - 10 mol % of spiroaminoborate ester 1 with different borane sources to afford non-racemic alcohols in up to 99% ee. In addition, modest enantioselectivity, around 80% ee, was achieved in the reduction of linear α,β-unsaturated heteroaryl ketones.

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Figures

Figure 1
Figure 1
Biologically active heterocyclic compounds containing sulfur.
Scheme 1
Scheme 1
See this image and copyright information in PMC

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