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Synthesis of Highly Substituted Methylenecyclohexenes Using New Domino Reactions with Sultones
Author(s) -
Plietker Bernd,
Seng Dieter,
Fröhlich Roland,
Metz Peter
Publication year - 2001
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 - 10.1002/1099-0690(200110)2001:19<3669::aid-ejoc3669>3.0.co;2-s
Subject(s) - chemistry , deprotonation , alkylation , silylation , transmetalation , trimethylsilane , allylic rearrangement , organic chemistry , magnesium bromide , medicinal chemistry , magnesium , catalysis , ion
New methods for the synthetic elaboration of sultones with concomitant desulfurization have been developed. Alkylation of sultones with (iodomethyl)trimethylsilane followed by treatment of the resultant silyl compound with tetrabutylammonium fluoride gave rise to sulfur‐free methylenecyclohexenes. In a more straightforward fashion, highly substituted compounds of the latter type were readily accessible by alkylation of α‐metallated allylic sultones prepared either by deprotonation, radical cyclization/transmetallation, or conjugate 1,6‐addition with (iodomethyl)magnesium chloride in a one‐pot transformation. An advanced intermediate for the synthesis of several 1,10‐ seco ‐eudesmanolides was rapidly constructed using such a protocol.