高对映选择性地将苯乙炔加成到脂肪族和芳香族醛上。
Highly enantioselective phenylacetylene additions to both aliphatic and aromatic aldehydes.
作者信息
Gao Ge, Moore David, Xie Ru-Gang, Pu Lin
机构信息
Department of Chemistry, University of Virginia, Charlottesville, VA 22904-4319, USA.
出版信息
Org Lett. 2002 Nov 14;4(23):4143-6. doi: 10.1021/ol026921r.
The readily available and inexpensive BINOL in combination with Ti(O(i)Pr)(4) is found to catalyze the reaction of an alkynylzinc reagent with various types of aldehydes including aliphatic aldehydes, aromatic aldehydes, and other alpha,beta-unsaturated aldehydes to generate chiral propargyl alcohols with 91-99% ee at room temperature. No previous chiral catalysts have exhibited such a broad scope of enantioselectivity with respect to the type of aldehydes for this reaction. [reaction: see text]
人们发现，容易获得且价格低廉的联萘酚（BINOL）与四异丙氧基钛（Ti(O(i)Pr)(4)）组合，能在室温下催化炔基锌试剂与各类醛（包括脂肪醛、芳香醛以及其他α,β-不饱和醛）反应，生成对映体过量值（ee）为91 - 99%的手性炔丙醇。就该反应中醛的类型而言，此前尚无手性催化剂表现出如此广泛的对映选择性范围。[反应：见正文]
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