Polyol synthesis through hydrocarbon oxidation: De novo synthesis of L-galactose

Dustin J. Covell; Nicolaas A. Vermeulen; Nathan A. Labenz; M. Christina White

doi:10.1002/anie.200603321

Polyol synthesis through hydrocarbon oxidation: De novo synthesis of L-galactose

Dustin J. Covell, Nicolaas A. Vermeulen, Nathan A. Labenz, M. Christina White

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

Abstract

(Chemical Equation Presented) Carbohydrates from hydrocarbons : A hydrocarbon oxidation strategy for the synthesis of chiral polyols is validated by the enantioselective, de novo synthesis of differentially protected L-galactose (see scheme, TBS = tert-butyldimethylsilyl, Bn = benzyl). Key to this strategy is the selective C-H oxidation method for transforming protected chiral allylic alcohols into (E)-2-butene-1,4-diol derivatives.

Original language	English (US)
Pages (from-to)	8217-8220
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	45
Issue number	48
DOIs	https://doi.org/10.1002/anie.200603321
State	Published - Dec 11 2006

Keywords

Allylic oxidation
C-H activation
Carbohydrates
Enantioselectivity
Polyols

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.200603321

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title = "Polyol synthesis through hydrocarbon oxidation: De novo synthesis of L-galactose",

abstract = "(Chemical Equation Presented) Carbohydrates from hydrocarbons : A hydrocarbon oxidation strategy for the synthesis of chiral polyols is validated by the enantioselective, de novo synthesis of differentially protected L-galactose (see scheme, TBS = tert-butyldimethylsilyl, Bn = benzyl). Key to this strategy is the selective C-H oxidation method for transforming protected chiral allylic alcohols into (E)-2-butene-1,4-diol derivatives.",

keywords = "Allylic oxidation, C-H activation, Carbohydrates, Enantioselectivity, Polyols",

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year = "2006",

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T1 - Polyol synthesis through hydrocarbon oxidation

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AU - Covell, Dustin J.

AU - Vermeulen, Nicolaas A.

AU - Labenz, Nathan A.

AU - White, M. Christina

PY - 2006/12/11

Y1 - 2006/12/11

N2 - (Chemical Equation Presented) Carbohydrates from hydrocarbons : A hydrocarbon oxidation strategy for the synthesis of chiral polyols is validated by the enantioselective, de novo synthesis of differentially protected L-galactose (see scheme, TBS = tert-butyldimethylsilyl, Bn = benzyl). Key to this strategy is the selective C-H oxidation method for transforming protected chiral allylic alcohols into (E)-2-butene-1,4-diol derivatives.

AB - (Chemical Equation Presented) Carbohydrates from hydrocarbons : A hydrocarbon oxidation strategy for the synthesis of chiral polyols is validated by the enantioselective, de novo synthesis of differentially protected L-galactose (see scheme, TBS = tert-butyldimethylsilyl, Bn = benzyl). Key to this strategy is the selective C-H oxidation method for transforming protected chiral allylic alcohols into (E)-2-butene-1,4-diol derivatives.

KW - Allylic oxidation

KW - C-H activation

KW - Carbohydrates

KW - Enantioselectivity

KW - Polyols

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Polyol synthesis through hydrocarbon oxidation: De novo synthesis of L-galactose

Abstract

Keywords

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