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New and Efficient Chiral Selenium Electrophiles
Author(s) -
Uehlin Lars,
Fragale Gianfranco,
Wirth Thomas
Publication year - 2002
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20020301)8:5<1125::aid-chem1125>3.0.co;2-i
Subject(s) - electrophile , selenium , chemistry , combinatorial chemistry , computer science , organic chemistry , catalysis
New chiral diselenides were prepared in a few steps from readily available starting materials. The selenium electrophiles generated from these diselenides were used for the efficient stereoselective inter‐ and intramolecular functionalization of alkenes. The substitution pattern influences the stereoselectivities and protection of the hydroxy moiety in the chiral side chain led to increased selectivities and yields in the selenenylation reactions. An additional substituent in the second ortho position was advantageous as well. Addition products with up to 96 % de were obtained. The influence of the nucleophile on the outcome of selenenylations of alkenes was studied to some extent as well.