Enantioselective Synthesis of Allylboronates and Allylic Alcohols by Copper??Catalyzed 1, 6??Boration

Y Luo, ID Roy, AGE Madec…

Index: Luo, Yunfei; Roy, Iain D.; Madec, Amael G. E.; Lam, Hon Wai Angewandte Chemie - International Edition, 2014 , vol. 53, # 16 p. 4186 - 4190

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Citation Number: 29

Abstract

Abstract Chiral secondary allylboronates are obtained in high enantioselectivities and 1, 6: 1, 4 ratios by the copper-catalyzed 1, 6-boration of electron-deficient dienes with bis (pinacolato) diboron (B 2 (pin) 2). The reactions proceed efficiently using catalyst loadings as low as 0.0049 mol%. The allylboronates may be oxidized to the allylic alcohols, and can be used in stereoselective aldehyde allylborations. This process was applied to a concise ...