α,α-Disubstituted Allyl Sulfones: An approach to the synthesis of vinyl-branched pheromone analogues

Autor:	Michal Hoskovec, Bohumír Koutek, Josef Lazar, Blanka Kalinová, Eva Brožová, Ludvík Streinz, Jan Vrkoč
Rok vydání:	1994
Předmět:	Singlet oxygen Organic Chemistry Alkylation Biochemistry Catalysis Sulfone Inorganic Chemistry chemistry.chemical_compound chemistry Yield (chemistry) Drug Discovery Organic chemistry Reactivity (chemistry) Physical and Theoretical Chemistry
Zdroj:	Helvetica Chimica Acta. 77:1281-1287
ISSN:	0018-019X
DOI:	10.1002/hlca.19940770510
Popis:	The two-step alkylation of phenyl prop-2-enyl sulfone (1) with protected ω-bromoalkanols and 1-iodoalkanes (3; see Scheme 1) followed by a Pd-catalyzed desulfonylation with LiBH4 affords a 96:4 mixture of vinylbranched, protected alcohols and corresponding ethylidene-branched isomers (see Scheme 2; 4 and 5, respectively). By utilizing the large difference in reactivity of mono- and trisubstituted CC bonds towards singlet oxygen, the ethylidene derivatives are easily removed from the mixture by photo-oxygenation. The vinyl-branched compounds are inert to this reaction and can be conveniently isolated in highly pure form (99.5%) and ca. 45% overall yield.
Databáze:	OpenAIRE
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