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铑催化的氧杂苯并降冰片二烯和氮杂苯并降冰片二烯的不对称环二聚反应:范围与局限

Rhodium-catalyzed asymmetric cyclodimerization of oxabenzonorbornadienes and azabenzonorbornadienes: scope and limitations.

作者信息

Allen Anna, Le Marquand Paul, Burton Ryan, Villeneuve Karine, Tam William

机构信息

Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, Ontario, Canada N1G 2W1.

出版信息

J Org Chem. 2007 Oct 12;72(21):7849-57. doi: 10.1021/jo7012884. Epub 2007 Sep 20.

DOI:10.1021/jo7012884
PMID:17880240
Abstract

Cationic rhodium(I)-catalyzed cyclodimerization of oxabenzonorbornadienes produced naphtho[1,2-b]furan ring systems in a single step with excellent yields and excellent enantioselectivities. The effect of various Rh(I) catalysts, Ag(I) salts, solvents, and phosphine ligands on the yield and enantioselectivity of the reaction was investigated, and the scope and limitations of this reaction with various oxabicyclic alkenes were studied. Similar results were obtained with the azabenzonorbornadiene analogues, providing the corresponding cyclodimerization products in excellent yields and excellent enantioselectivities.

摘要

阳离子铑(I)催化的氧杂苯并降冰片二烯的环二聚反应一步生成萘并[1,2 - b]呋喃环系,产率和对映选择性优异。研究了各种铑(I)催化剂、银(I)盐、溶剂和膦配体对反应产率和对映选择性的影响,并研究了该反应与各种氧杂双环烯烃反应的范围和局限性。氮杂苯并降冰片二烯类似物也得到了类似的结果,以优异的产率和对映选择性提供了相应的环二聚产物。

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