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Silicon‐Directed Nazarov Cyclizations. Part V. Substituent and heteroatom effects on the reaction
Author(s) -
Denmark Scott E.,
Habermas Karl L.,
Hite Gary A.
Publication year - 1988
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19880710120
Subject(s) - chemistry , heteroatom , substituent , ketone , cyclobutane , alkyl , aryl , medicinal chemistry , bicyclic molecule , stereochemistry , organic chemistry , ring (chemistry)
The ability to incorporate alkyl, alkenyl, aryl, and heteroatomic groups into substrates for the silicon‐directed Nazarov cyclization and their subsequent reactions has been investigated. In general, most of the groups are compatible with the conditions for the cyclization and do not interfere even when directly attached to the divinyl ketone. The influence of substituents on the rate of the cyclization has been addressed and is consistent with a simple mechanistic picture. O‐ and N‐Containing functions are tolerated except when attached to the α‐vinyl C‐atom of the divinyl ketone. The diastereoface‐directing effect of a fused cyclobutane is discussed.