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A relay ring-closing metathesis synthesis of dihydrooxasilines, precursors of (Z)-iodo olefins.

ABSTRACT: A convenient Grubbs II metathesis provides dihydrooxasilines by relay RCM (RRCM). Dihydrooxasilines undergo ring opening to give Z-vinyl silanes. These can then be converted to Z-vinyl iodides. This sequence provides a short, high yield, and convenient route to trisubstituted Z-vinyl iodides, useful intermediates for the preparation of polypropionate antibiotics.

SUBMITTER: Xie Q

PROVIDER: S-EPMC2765515 | biostudies-literature | 2008 Dec

REPOSITORIES: biostudies-literature

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A relay ring-closing metathesis synthesis of dihydrooxasilines, precursors of (Z)-iodo olefins.

Xie Qiuzhe Q Denton Richard W RW Parker Kathlyn A KA

Organic letters 20081201 23

A convenient Grubbs II metathesis provides dihydrooxasilines by relay RCM (RRCM). Dihydrooxasilines undergo ring opening to give Z-vinyl silanes. These can then be converted to Z-vinyl iodides. This sequence provides a short, high yield, and convenient route to trisubstituted Z-vinyl iodides, useful intermediates for the preparation of polypropionate antibiotics. ...[more]

PMID: 19006314

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