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A new chiral auxiliary for asymmetric thermal reactions: High stereocontrol in radical addition, allylation, and annulation reactions

JG Stack, DP Curran, SV Geib, J Rebek Jr…

文献索引:Stack, Jeffrey G.; Curran, Dennis P.; Geib, Steven V.; Rebek Jr., Julius; Ballester, Pablo Journal of the American Chemical Society, 1992 , vol. 114, # 18 p. 7007 - 7018

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被引用次数: 102

摘要

Abstract: A new imide chiral auxiliary, endo-7-(2-benzoxazolyl)-l, 5, 7-trimethyl-3-azabicyclo [3.3. l] nonan-2-one (5), is prepared from Kemp's triacid and resolved via its menthyl carbamate. Mixed fumarate derivatives of the auxiliary show unprecedented control of regiochemistry and@-stereochemistry in representative radical addition reactions. Chiral radicals derived from 5 also show extremely high levels of stereoselectivity in ...