Rapid preparation of variously protected glycals using titanium(III)

Roxanne P. Spencer, Cullen L. Cavallaro, Jeffrey Schwartz

Research output: Contribution to journalArticle

49 Scopus citations

Abstract

Glycosyl chlorides and bromides can be rapidly converted to glycals in high yield by reaction with (Cp2Ti[III]Cl)2. This reagent tolerates a wide range of common carbohydrate protecting groups, including silyl ethers, acetals, and esters; the methodology provides a general route for the preparation of glycals substituted with both acid- and base-labile functionality. A reaction mechanism is proposed that is based on heteroatom abstraction to give an intermediate glycosyl radical. This radical reacts with a second equivalent of Ti(III) to yield a glycosyltitanium(IV) species. β-Heteroatom elimination from the glycosyltitanium(IV) complex gives the glycal.

Original languageEnglish (US)
Pages (from-to)3987-3995
Number of pages9
JournalJournal of Organic Chemistry
Volume64
Issue number11
DOIs
StatePublished - May 28 1999

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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