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Syntheses of α, β‐Epoxy Silyl Ketones
Author(s) -
Scheller Markus E.,
Bernd Schweizer W.,
Frei Bruno
Publication year - 1989
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.19890720210
Subject(s) - silylation , chemistry , epoxy , reagent , pyridine , allylic rearrangement , alcohol , allylic alcohol , medicinal chemistry , organic chemistry , crystal structure , catalysis , polymer chemistry
The synthesis of the α, β‐epoxy‐acylsilanes 1 and 2 starting from the allylic silyl alcohols ( E )‐ and ( Z )‐ 3 , respectively, by epoxidation with t ‐BuOOH/VO(acac) 2 followed by oxidation with Collins reagent (CrO 3 /pyridine) in up to 70% overall yields, is described. The acid‐catalyzed rearrangement of the epoxy‐silyl alcohols 4A + B und 5A + B led to the novel unstable diastereoisomeric α‐silyl‐β‐hydroxy‐aldehydes 9 and 10 , respectively. The structure of 10 was established by X‐ray crystal‐structure analysis of the corresponding alcohol 11 .