Oxazolidine Synthesis by Complementary Stereospecific and Stereoconvergent Methods
Oxazolidine Synthesis by Complementary Stereospecific and Stereoconvergent Methods
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DOI：
10.1021/ol202068p
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发表时间：
2011-10-07
期刊：
影响因子：
5.2
通讯作者：
Jarvo, Elizabeth R.
中科院分区：
文献类型：
--
作者：
Shaghafi, Michael B.;Grote, Robin E.;Jarvo, Elizabeth R.
报道了互补立体定向和立体会聚反应对映选择性合成1，3-恶唑烷。在铑催化剂存在下，对映体富集的一氧化丁二烯与芳基亚胺的反应是立体专一的（99%ee）。或者，在手性钯或镍催化剂存在下，外消旋丁二烯一氧化物的反应提供了1，3-恶唑烷的对映选择性合成（高达94%ee）。顺式或反式-1，3-恶唑烷的合成也在催化剂控制下完成。
Complementary stereospecific and stereoconvergent reactions for enantioselective synthesis of 1,3-oxazolidines are reported. In the presence of a rhodium catalyst, reaction of enantioenriched butadiene monoxide with aryl imines is stereospecific (99% ee). Alternatively, the reaction of racemic butadiene monoxide, in the presence of a chiral palladium or nickel catalyst, provides an enantioselective synthesis of 1,3-oxazolidines (up to 94% ee). Synthesis of either the cis- or trans-1,3-oxazolidines is also accomplished under catalyst control.