Chiral silyl ketene acetals from thioesters: Reaction with acetals and peroxyacetals to form 3-alkoxy- and 3-peroxyalkanoates

Patrick H. Dussault; Tony K. Trullinger; Su Cho-Shultz

doi:10.1016/S0040-4020(00)00894-2

Chiral silyl ketene acetals from thioesters: Reaction with acetals and peroxyacetals to form 3-alkoxy- and 3-peroxyalkanoates

Patrick H. Dussault, Tony K. Trullinger, Su Cho-Shultz

Research output: Contribution to journal › Article › peer-review

18 Scopus citations

Abstract

The Lewis acid-mediated reaction of chiral O- and S-silyl ketene acetals (SKAs) with peroxyacetals and acetals was investigated as an approach to the asymmetric synthesis of 3-peroxy- and 3-alkoxyalkanoates. SKAs derived from chiral O-acetates fail to react with peroxyacetals and provide little diastereoselection in reactions of nonperoxidic acetals. Reaction of thioacetate SKAs with peroxyacetals furnishes 3-peroxyalkanoate thioesters in good yield but with poor diastereoselection. In the case of silyl ketene acetals based upon a camphorsulfonamide chiral auxiliary the diastereomeric peroxyalkanoates are easily separated. (C) 2000 Elsevier Science Ltd.

Original language	English (US)
Pages (from-to)	9213-9220
Number of pages	8
Journal	Tetrahedron
Volume	56
Issue number	47
DOIs	https://doi.org/10.1016/S0040-4020(00)00894-2
State	Published - Nov 17 2000

Keywords

Chiral auxiliary
Peroxide
Silyl ketene acetal
Thioester

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(00)00894-2

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@article{96d7a57f97214512aa9b89829e8880bd,

title = "Chiral silyl ketene acetals from thioesters: Reaction with acetals and peroxyacetals to form 3-alkoxy- and 3-peroxyalkanoates",

abstract = "The Lewis acid-mediated reaction of chiral O- and S-silyl ketene acetals (SKAs) with peroxyacetals and acetals was investigated as an approach to the asymmetric synthesis of 3-peroxy- and 3-alkoxyalkanoates. SKAs derived from chiral O-acetates fail to react with peroxyacetals and provide little diastereoselection in reactions of nonperoxidic acetals. Reaction of thioacetate SKAs with peroxyacetals furnishes 3-peroxyalkanoate thioesters in good yield but with poor diastereoselection. In the case of silyl ketene acetals based upon a camphorsulfonamide chiral auxiliary the diastereomeric peroxyalkanoates are easily separated. (C) 2000 Elsevier Science Ltd.",

keywords = "Chiral auxiliary, Peroxide, Silyl ketene acetal, Thioester",

author = "Dussault, {Patrick H.} and {K. Trullinger}, Tony and Su Cho-Shultz",

note = "Funding Information: We thank the NIH for financial support, Professor Richard Shoemaker for assistance with NMR experiments, and Dr John Desper for obtaining the crystal structure of the dioxolane.",

year = "2000",

month = nov,

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doi = "10.1016/S0040-4020(00)00894-2",

language = "English (US)",

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pages = "9213--9220",

journal = "Tetrahedron",

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T1 - Chiral silyl ketene acetals from thioesters

T2 - Reaction with acetals and peroxyacetals to form 3-alkoxy- and 3-peroxyalkanoates

AU - Dussault, Patrick H.

AU - K. Trullinger, Tony

AU - Cho-Shultz, Su

N1 - Funding Information: We thank the NIH for financial support, Professor Richard Shoemaker for assistance with NMR experiments, and Dr John Desper for obtaining the crystal structure of the dioxolane.

PY - 2000/11/17

Y1 - 2000/11/17

N2 - The Lewis acid-mediated reaction of chiral O- and S-silyl ketene acetals (SKAs) with peroxyacetals and acetals was investigated as an approach to the asymmetric synthesis of 3-peroxy- and 3-alkoxyalkanoates. SKAs derived from chiral O-acetates fail to react with peroxyacetals and provide little diastereoselection in reactions of nonperoxidic acetals. Reaction of thioacetate SKAs with peroxyacetals furnishes 3-peroxyalkanoate thioesters in good yield but with poor diastereoselection. In the case of silyl ketene acetals based upon a camphorsulfonamide chiral auxiliary the diastereomeric peroxyalkanoates are easily separated. (C) 2000 Elsevier Science Ltd.

AB - The Lewis acid-mediated reaction of chiral O- and S-silyl ketene acetals (SKAs) with peroxyacetals and acetals was investigated as an approach to the asymmetric synthesis of 3-peroxy- and 3-alkoxyalkanoates. SKAs derived from chiral O-acetates fail to react with peroxyacetals and provide little diastereoselection in reactions of nonperoxidic acetals. Reaction of thioacetate SKAs with peroxyacetals furnishes 3-peroxyalkanoate thioesters in good yield but with poor diastereoselection. In the case of silyl ketene acetals based upon a camphorsulfonamide chiral auxiliary the diastereomeric peroxyalkanoates are easily separated. (C) 2000 Elsevier Science Ltd.

KW - Chiral auxiliary

KW - Peroxide

KW - Silyl ketene acetal

KW - Thioester

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U2 - 10.1016/S0040-4020(00)00894-2

DO - 10.1016/S0040-4020(00)00894-2

M3 - Article

AN - SCOPUS:0034680673

SN - 0040-4020

VL - 56

SP - 9213

EP - 9220

JO - Tetrahedron

JF - Tetrahedron

IS - 47

ER -

Chiral silyl ketene acetals from thioesters: Reaction with acetals and peroxyacetals to form 3-alkoxy- and 3-peroxyalkanoates

Abstract

Keywords

ASJC Scopus subject areas

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