Regioselective alkyl and alkynyl substitution reactions of epoxy alcohols by the use of organoaluminum ate complexes: regiochemical reversal of nucleophilic substitution reactions.
Regioselective alkyl and alkynyl substitution reactions of epoxy alcohols by the use of organoaluminum ate complexes: regiochemical reversal of nucleophilic substitution reactions.
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DOI：
10.1021/ol010062
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发表时间：
2001-04
期刊：
影响因子：
5.2
通讯作者：
M. Sasaki;K. Tanino;M. Miyashita
中科院分区：
文献类型：
--
作者：
M. Sasaki;K. Tanino;M. Miyashita
已经研究了2，3-环氧-1-烷醇与烷基-和炔基铝酸盐络合物的前所未有的亲核取代反应，并证明其以极高的立体选择性发生在C2位，即，与用常规有机铝试剂进行的取代反应中获得的区域选择性正好相反，导致以优异的产率形成C2-烷基和C2-炔基取代产物。
Unprecedented nucleophilic substitution reactions of 2,3-epoxy-1-alkanols with alkyl- and alkynylaluminum ate complexes have been studied and demonstrated to occur at the C2 position with extremely high stereoselectivity, i.e., with exactly reversed regioselectivity to that obtained in the substitution reactions by normal organoaluminum reagents, resulting in the formation of the C2-alkyl and C2-alkynyl substitution products in excellent yields.