2-B（取代的烯丙基）醇的非对映选择性氮丙啶化：新型有机硼化合物的有效方法。
Diastereoselective aziridination of 2-B(pin)-substituted allylic alcohols: an efficient approach to novel organoboron compounds.
机构信息
P. Roy and Diana T. Vagelos Laboratories, University of Pennsylvania, Department of Chemistry, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
出版信息
Org Lett. 2011 Nov 18;13(22):6094-7. doi: 10.1021/ol202588g. Epub 2011 Oct 25.
Abstract
We report that 2-B(pin)-substituted allylic alcohols are good substrates for diastereoselective aziridinations in the presence of PhI(OAc)(2) and N-aminophthalimide. Under the aziridination conditions, the valuable B-C bond remains intact, affording a variety of novel boron-substituted aziridines in good yields and excellent diastereoselectivities. Oxidation of the aziridine B-C bond enables generation of syn-1,3-aminohydroxy-2-ketones with high diastereoselectivity.
摘要
我们报告称，2-B（取代基）烯丙醇在 PhI(OAc)2 和 N-氨基邻苯二甲酰亚胺的存在下是立体选择性氮丙啶化的良好底物。在氮丙啶化条件下，有价值的 B-C 键保持完整，以高收率和优异的立体选择性得到各种新型硼取代氮丙啶。氮丙啶 B-C 键的氧化可生成具有高立体选择性的顺式-1,3-氨基羟基-2-酮。
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