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Lewis Base Catalyzed 1,3‐Dithiane Addition to Carbonyl and Imino Compounds Using 2‐Trimethylsilyl‐1,3‐dithiane
Author(s) -
Michida Makoto,
Mukaiyama Teruaki
Publication year - 2008
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200800091
Subject(s) - dithiane , aldimine , chemistry , trimethylsilyl , lewis acids and bases , electrophile , catalysis , adduct , medicinal chemistry , base (topology) , organic chemistry , mathematical analysis , mathematics
Lewis base‐catalyzed 1,3‐dithiane addition to electrophiles such as carbonyl compounds and N‐ substituted aldimines with 2‐trimethylsilyl‐1,3‐dithiane (TMS‐dithiane) is described. By the activation of the carbon‐silicon bond in the presence of a Lewis base catalyst such as tetrabutylammonium phenoxide (PhON n Bu 4 ), a 1,3‐dithiane addition reaction proceeded smoothly to afford the corresponding adducts in good to high yields under mild conditions. This synthesis is also applied to the reactions of ketones having α‐ protons, and of N‐ substituted aldimines.