The carbo-metallation of allylic alcohols : scope, stereochemistry, and a synthesis of a precursor to Tsukubaenolide (FK-506)
The carbo-metallation of allylic alcohols : scope, stereochemistry, and a synthesis of a precursor to Tsukubaenolide (FK-506)
The intermolecular carbometallation of several allylic alcohols, in particular (E)-4-trimethylsily-3-buten-2-ol, has been studied to determine and increase the stereochemical control, scope, and efficiency of this reaction. Allyl magnesiation has been by far the most successful, but important advances have been made for other organometallics. The organometallic reagents formed as a result of allyl magnesiation have been quenched with a variety of electrophiles to form synthetically useful compounds, and hence the use of an allyl alcohol as a -C-+C-CHR(OH) synthetic equivalent has been developed. The allyl magnesiation and then carbon dioxide quenching of (E)-4-trimethylsily-3-buten-2-ol has been applied to the synthesis of t-4-allyl-r-5-methyl-2-trimethylstannyl-4,5-dihydrofuran, which was required by this group for the synthesis of Tsukubaenolide (FK-506).
University of Southampton
1990
Love, Christopher John
(1990)
The carbo-metallation of allylic alcohols : scope, stereochemistry, and a synthesis of a precursor to Tsukubaenolide (FK-506).
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
The intermolecular carbometallation of several allylic alcohols, in particular (E)-4-trimethylsily-3-buten-2-ol, has been studied to determine and increase the stereochemical control, scope, and efficiency of this reaction. Allyl magnesiation has been by far the most successful, but important advances have been made for other organometallics. The organometallic reagents formed as a result of allyl magnesiation have been quenched with a variety of electrophiles to form synthetically useful compounds, and hence the use of an allyl alcohol as a -C-+C-CHR(OH) synthetic equivalent has been developed. The allyl magnesiation and then carbon dioxide quenching of (E)-4-trimethylsily-3-buten-2-ol has been applied to the synthesis of t-4-allyl-r-5-methyl-2-trimethylstannyl-4,5-dihydrofuran, which was required by this group for the synthesis of Tsukubaenolide (FK-506).
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Published date: 1990
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Local EPrints ID: 458305
URI: http://eprints.soton.ac.uk/id/eprint/458305
PURE UUID: acf1d78a-1555-4fda-8316-cc5c5a9537b0
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Date deposited: 04 Jul 2022 16:46
Last modified: 04 Jul 2022 16:46
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Author:
Christopher John Love
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