Enantioselective silyl protection of alcohols catalysed by an amino-acid-based small molecule

被引:177
作者
Zhao, Yu [1 ]
Rodrigo, Jason [1 ]
Hoveyda, Amir H. [1 ]
Snapper, Marc L. [1 ]
机构
[1] Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1038/nature05102
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
Reliable, selective and environmentally friendly chemical transformations are crucial to the development of new therapeutics and the design of novel materials. Chiral catalysts that can be easily prepared and used to obtain organic molecules of high enantiomeric purity are critical to modern chemical synthesis(1). The development of protecting groups that shield reactive functionalities has also proved indispensable in the preparation of complex biologically active molecules(2). Here we present a chiral catalyst that promotes the enantioselective protection of a secondary alcohol as one of the most commonly used protected forms of an alcohol: a silyl ether. The catalyst is a small, simple molecule that can be prepared in three steps from commercial materials without the need for rigorously controlled conditions. Enantioselective silylations are performed with commercial silyl chlorides and produce yields of up to 96 per cent at an enantiomeric ratio of up to 98:2. Chiral catalysts for selective formation of commonly used protecting groups such as silyl ethers should significantly enhance the ability of chemical synthesis to deliver, in a more practical and efficient manner, important organic molecules.
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页码:67 / 70
页数:4
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