Preparation and synthetic utility of oxasilacyclopentane acetals derived from siliranes

Jared T. Shaw; K. A. Woerpel

doi:10.1016/S0040-4020(97)01039-9

Preparation and synthetic utility of oxasilacyclopentane acetals derived from siliranes

Jared T. Shaw, K. A. Woerpel

Chemistry

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

Abstract

The insertion of formamides into a C-Si bond of silirane trans- 1 provides a facile route to the oxasilacyclopentane acetate 5 (86% overall yield). Stereoselective carbon-carbon bond formation on the derived oxonium ion was achieved by addition of the silyl enol ether of acetophenone (92:8 selectivity, 79% yield) and 3-pentanone (92:5:3 selectivity, 100% yield). These results demonstrate the potential of siliranes as intermediates in organic synthesis.

Original language	English (US)
Pages (from-to)	16597-16606
Number of pages	10
Journal	Tetrahedron
Volume	53
Issue number	48
DOIs	https://doi.org/10.1016/S0040-4020(97)01039-9
State	Published - Dec 1 1997

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(97)01039-9

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abstract = "The insertion of formamides into a C-Si bond of silirane trans- 1 provides a facile route to the oxasilacyclopentane acetate 5 (86% overall yield). Stereoselective carbon-carbon bond formation on the derived oxonium ion was achieved by addition of the silyl enol ether of acetophenone (92:8 selectivity, 79% yield) and 3-pentanone (92:5:3 selectivity, 100% yield). These results demonstrate the potential of siliranes as intermediates in organic synthesis.",

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N2 - The insertion of formamides into a C-Si bond of silirane trans- 1 provides a facile route to the oxasilacyclopentane acetate 5 (86% overall yield). Stereoselective carbon-carbon bond formation on the derived oxonium ion was achieved by addition of the silyl enol ether of acetophenone (92:8 selectivity, 79% yield) and 3-pentanone (92:5:3 selectivity, 100% yield). These results demonstrate the potential of siliranes as intermediates in organic synthesis.

AB - The insertion of formamides into a C-Si bond of silirane trans- 1 provides a facile route to the oxasilacyclopentane acetate 5 (86% overall yield). Stereoselective carbon-carbon bond formation on the derived oxonium ion was achieved by addition of the silyl enol ether of acetophenone (92:8 selectivity, 79% yield) and 3-pentanone (92:5:3 selectivity, 100% yield). These results demonstrate the potential of siliranes as intermediates in organic synthesis.

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ER -

Preparation and synthetic utility of oxasilacyclopentane acetals derived from siliranes

Abstract

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