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- Title
Diastereoselective Nucleophilic Ring-Opening Reactions of 2,6-Diazasemibullvalenes for the Synthesis of Diverse Functionalized Δ<sup>1</sup>-Bipyrroline Derivatives.
- Authors
Zhang, Shaoguang; Zhan, Ming; Zhang, Wen‐Xiong; Xi , Zhenfeng
- 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.
- Subjects
NUCLEOPHILES; CARBOXYLIC acids; ENOLS; NUCLEOPHILIC addition (Chemistry); ALCOHOLS (Chemical class); YLIDES
- Publication
Chemistry - A European Journal, 2014, Vol 20, Issue 31, p9744
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201402911