Anti and Syn Glycolate Aldol Reactions with a Readily Displaced Thiol Auxiliary

S. Fanjul, A. N. Hulme

Research output: Contribution to journalArticlepeer-review

Abstract

The TBDPS protected glycolate derivative of thiol auxiliary 1 is readily prepared (3 steps, 80% overall yield) and has been shown to give excellent anti:syn selectivity (>97:3) and high facial selectivity (88:12 to 97:3) in glycolate aldol reactions with a range of aldehydes (75-87% isolated yield major diastereomer). In contrast, its benzyl protected counterpart displays more versatility with respect to the generation
of either anti or syn glycolate aldol adducts, but only modest facial selectivity. The thiol auxiliary has been shown to be readily displaced under mild conditions to give alcohol and ester derivatives of the glycolate aldol adducts.
Original languageEnglish
Pages (from-to)9788-9791
Number of pages4
JournalJournal of Organic Chemistry
Volume73
Issue number24
DOIs
Publication statusPublished - Dec 2008

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