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Asymmetric Addition Reactions with Optimized Selenium Electrophiles
Author(s) -
Wirth Thomas,
Fragale Gianfranco
Publication year - 1997
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/chem.19970031123
Subject(s) - electrophile , selenium , diastereomer , moiety , chemistry , selectivity , styrene , electrophilic addition , addition reaction , optically active , organic chemistry , combinatorial chemistry , catalysis , polymer , copolymer
Abstract The synthesis of various nonracemic diselenides by different methods is described. These diselenides are precursors for optically active selenium electrophiles. Their facial selectivity upon addition to styrene was investigated with respect to the chiral moiety neighboring the selenium. Diselenides 1 i, 1 n , and 1 v yielded addition products 7 with diastereomeric excesses up to 95%. Some diselenides, intermediates, and products of the addition reaction were investigated by 77 Se NMR spectroscopy.