Synthesis of homoallylic chiral tertiary alcohols via chelation-controlled diastereoselective nucleophilic addition on α-alkoxyketones: Application for the synthesis of the C1-C11 subunit of 8-epi-fostriecin

P. Veeraraghavan Ramachandran; Haipeng Liu; M. Venkat Ram Reddy; Herbert C. Brown

doi:10.1021/ol035516c

Synthesis of homoallylic chiral tertiary alcohols via chelation-controlled diastereoselective nucleophilic addition on α-alkoxyketones: Application for the synthesis of the C₁-C₁₁ subunit of 8-epi-fostriecin

P. Veeraraghavan Ramachandran, Haipeng Liu, M. Venkat Ram Reddy, Herbert C. Brown

Chemistry & Biochemistry

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

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Abstract

(Matrix presented) Chiral β-syn-alkoxyhomoallylic alcohols derived from alkoxyallylboration of aldehydes upon oxidation provided the corresponding chiral ketones. Chelation-controlled nucleophilic addition to these ketones occurred in a highly stereoselective manner to afford anti-homoallylic tertiary alcohols. This methodology has been applied for the synthesis of the C ₁-C₁₁ subunit of C₈-epi-fostriecin.

Original language	English (US)
Pages (from-to)	3755-3757
Number of pages	3
Journal	Organic Letters
Volume	5
Issue number	20
DOIs	https://doi.org/10.1021/ol035516c
State	Published - Oct 2 2003

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10.1021/ol035516c

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Synthesis of homoallylic chiral tertiary alcohols via chelation-controlled diastereoselective nucleophilic addition on α-alkoxyketones: Application for the synthesis of the C₁-C₁₁ subunit of 8-epi-fostriecin. / Ramachandran, P. Veeraraghavan; Liu, Haipeng; Reddy, M. Venkat Ram et al.
In: Organic Letters, Vol. 5, No. 20, 02.10.2003, p. 3755-3757.

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

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abstract = "(Matrix presented) Chiral β-syn-alkoxyhomoallylic alcohols derived from alkoxyallylboration of aldehydes upon oxidation provided the corresponding chiral ketones. Chelation-controlled nucleophilic addition to these ketones occurred in a highly stereoselective manner to afford anti-homoallylic tertiary alcohols. This methodology has been applied for the synthesis of the C 1-C11 subunit of C8-epi-fostriecin.",

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