Diastereoselective Nucleophilic Ring‐Opening Reactions of 2,6‐Diazasemibullvalenes for the Synthesis of Diverse Functionalized Δ1‐Bipyrroline Derivatives |
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| Authors: | Dr. Shaoguang Zhang Ming Zhan Prof. Dr. Wen‐Xiong Zhang Prof. Dr. Zhenfeng Xi |
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| Affiliation: | 1. 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;2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032 (P. R. China) |
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| 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 Δ1‐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. |
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| Keywords: | bipyrrolines diastereoselectivity Lewis acids nucleophiles ring opening |
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