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Synthesis of functionalized γ-lactone via Sakurai exo-cyclization/rearrangement of 3,3-bis(silyl) enol ester with a tethered acetal.
- Source :
-
Organic letters [Org Lett] 2015 Mar 20; Vol. 17 (6), pp. 1553-6. Date of Electronic Publication: 2015 Mar 02. - Publication Year :
- 2015
-
Abstract
- An efficient synthesis of functionalized γ-lactones has been developed involving Sakurai exo-cyclization/rearrangement of 3,3-bis(silyl) enol esters with a tethered acetal. While the steric and electronic effects of geminal bis(silane) favor the desired Sakurai pathway, the methoxy species formed in the deprotection step also facilitates both cyclization and rearrangement. The synthetic value of this approach has been demonstrated by efficiently transforming the E-vinylsilane into enyne and the γ-lactone moiety into multisubstituted THF.
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 17
- Issue :
- 6
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 25730288
- Full Text :
- https://doi.org/10.1021/acs.orglett.5b00437