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A Synthetic Approach to Tetrasubstituted Alkenes: Using β‐Carbonyl Benzothiazol‐2‐yl Sulfones as Electrophiles
Author(s) -
Ou Song,
Cao ChunRu,
Jiang Min,
Liu JinTao
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301021
Subject(s) - electrophile , chemistry , sulfone , yield (engineering) , alkoxy group , combinatorial chemistry , organic chemistry , medicinal chemistry , catalysis , alkyl , materials science , metallurgy
Abstract A novel olefination method based on the modified Julia olefination reaction was developed. The reactions of β‐carbonyl benzothiazol‐2‐yl sulfones with a series of alkynyllithiums and TMSCN gave the corresponding β‐alkoxy sulfone intermediates, which underwent facile Smiles rearrangement and spontaneous elimination to yield tetrasubstituted enynes and cyanoalkenes, respectively.