Menard Frederic, Chapman Timothy M, Dockendorff Chris, Lautens Mark
Davenport Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario, Canada M5H 3H6.
Org Lett. 2006 Sep 28;8(20):4569-72. doi: 10.1021/ol061777l.
An enantio-, regio-, and diastereoselective rhodium(I)-catalyzed desymmetrization of a meso-cyclic allylic dicarbonate with organoboronic acid nucleophiles is described. The rhodium(I) catalyst formed in situ from [Rh(cod)OH]2 and Xyl-P-PHOS allowed the S(N)2' allylic substitution product to be obtained with a range of arylboronic acids in enantiomeric excesses of up to 92% with regioselectivities of up to >20:1.
本文描述了一种铑（I）催化的内消旋环状烯丙基二碳酸酯与有机硼酸亲核试剂的对映、区域和非对映选择性去对称化反应。由[Rh(cod)OH]2和Xyl-P-PHOS原位生成的铑（I）催化剂，能使一系列芳基硼酸通过S(N)2'烯丙基取代反应得到对映体过量高达92%、区域选择性高达>20:1的产物。
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