One-pot synthesis of chiral bicyclo[3.3.0]octatrienes using diphenylprolinol silyl ether-mediated ene-type reaction

One-pot synthesis of chiral bicyclo[3.3.0]octatrienes using diphenylprolinol silyl ether-mediated ene-type reaction
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DOI:
10.1016/j.tet.2010.03.010
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发表时间:
2010-06-26
期刊:
影响因子:
2.1
通讯作者:
Hayashi, Yujiro
Hayashi, Yujiro
中科院分区:
化学3区
文献类型:
--
作者:
Gotoh, Hiroaki;Ogino, Hiroshi;Hayashi, Yujiro

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以α,β-不饱和醛和环戊二烯为起始原料,通过二苯基脯氨醇硅醚介导的烯型反应、环戊二烯与醛的分子内加成反应和脱水反应,一锅法合成了具有良好对映选择性的手性双环[3.3.0]辛三烯. (C)2010爱思唯尔有限公司版权所有。
Chiral bicyclo[3.3.0]octatrienes with excellent enantioselectivity were synthesized from the simple starting materials of alpha,beta-unsaturated aldehyde and cyclopentadiene via one-pot operation, which consisted of a diphenylprolinol silyl ether-mediated ene-type reaction, intramolecular addition reaction of cyclopentadiene moiety with aldehyde and dehydration reaction. (C) 2010 Elsevier Ltd. All rights reserved.