Asymmetric allyl-and crotylboration with the robust, versatile, and recyclable 10-TMS-9-borabicyclo [3.3. 2] decanes

…, E Canales, K Matos, JA Soderquist

Index: Burgos, Carlos H.; Canales, Eda; Matos, Karl; Soderquist, John A. Journal of the American Chemical Society, 2005 , vol. 127, # 22 p. 8044 - 8049

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Citation Number: 125

Abstract

The remarkable versatility and selectivity of the 10-(trimethylsilyl)-9-borabicyclo [3.3. 2] decanes (10-TMS-9-BBDs) in the allyl-and crotylboration of representative aldehydes are reported. The new reagents are prepared through air-stable crystalline pseudoephedrine borinic ester complexes of the 10-TMS-9-BBDs (4), which are available in 63% overall yield from B-MeO-9-BBN through a simple two-step procedure. These complexes 4 are directly ...