title: Diastereoselective nucleophilic ring-opening reactions of 2,6-diazasemibullvalenes for the synthesis of diverse functionalized δ(1) -bipyrroline derivatives.
abstract: Nucleophilic ring-opening reactions of 2,6-diazasemibullvalenes (NSBVs) were investigated. Different types of nucleophile (alcohols, phenols, thiols, carboxylic acids, water, enols, amines, indoles, metal-halide salts, sodium azide, organozinc compounds, lithium alkynethiolate, and sulfoxonium ylides) were used to afford diverse functionalized Δ(1) -bipyrroline derivatives in good yields with high regio- and diastereoselectivity. Most of the reactions featured milder conditions and higher reactivity relative to those for common aziridine derivatives, probably because of the rigid ring system and substitution patterns of NSBVs.
authors: Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871 (P.R. China), Fax: (+86) 10-62751708.
authors: Shaoguang
authors: S
authors: Zhang
authors: Ming
authors: M
authors: Zhan
authors: Wen-Xiong
authors: WX
authors: Zhang
authors: Zhenfeng
authors: Z
authors: Xi
keywords: Lewis acids; bipyrrolines; diastereoselectivity; nucleophiles; ring opening