Catalytic Enantioselective Allyl-and Crotylboration of Aldehydes Using Chiral Diol• SnCl4 Complexes. Optimization, Substrate Scope and Mechanistic Investigations

V Rauniyar, H Zhai, DG Hall

文献索引：Rauniyar, Vivek; Zhai, Huimin; Hall, Dennis G. Journal of the American Chemical Society, 2008 , vol. 130, # 26 p. 8481 - 8490

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被引用次数: 114

摘要

We report a novel class of C2-symmetric chiral diols derived from the hydrobenzoin skeleton. The combination of these diols with SnCl4 under Yamamoto's concept of Lewis acid assisted Brønsted acidity (LBA catalysis) leads to high levels of asymmetric induction in the allylboration of aldehydes by commercially available allylboronic acid pinacol ester 1a. The corresponding homoallylic alcohol products of synthetically useful aliphatic ...