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Regioselective and stereoselective cleavage of cis‐4‐methyl‐2‐vinyl‐l,3‐dioxane by alkyllithiums
Author(s) -
Bailey William F.,
Zarcone Lyn M.J.
Publication year - 2002
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10063
Subject(s) - chemistry , regioselectivity , alkoxide , stereoselectivity , substituent , enol , bond cleavage , cleavage (geology) , lithium (medication) , enol ether , stereochemistry , yield (engineering) , medicinal chemistry , organic chemistry , catalysis , medicine , materials science , geotechnical engineering , fracture (geology) , engineering , metallurgy , endocrinology
The reaction of alkyllithiums with cis ‐4‐methyl‐2‐vinyl‐1,3‐dioxane proceeds in virtually quantitative yield via a formal S N 2′ ring opening that proceeds in a regioselective manner to give preferential cleavage of the C(2)–O(l) bond remote from the 4‐methyl substituent, affording the E‐enol ether as the major stereoisomer. A two‐step mechanism, involving addition of the alkyllithium followed by syn ‐elimination of lithium alkoxide, is suggested to account for the stereochemical outcome. Chirality 14:163–165, 2002.© 2002 Wiley‐Liss, Inc.
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