Connective synthesis of polysubstituted tetrahydropyrans by a novel and stereocontrolled metallo-ene/Intramolecular Sakurai Cyclization sequence

DOI: 10.1021/jo025899c

Source and publish data:

Journal of Organic Chemistry p. 8744 - 8752 (2002)

Update date:2022-08-04

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Authors:

Leroy, Bernard

Marko, Istvan E.

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Article abstract of DOI:10.1021/jo025899c

A novel methodology based upon the allylmetalation step followed by an Intramolecular Sakurai Cyclization (IMSC) provides an efficient access to a variety of tetrahydropyran derivatives. This new strategy nicely complements our initial protocol that embodied a tandem ene reaction/IMSC sequence. Both mono- and dihydroxy-tetrahydropyrans could be easily assembled with complete stereocontrol at the various chiral centers.

Full text of DOI:10.1021/jo025899c

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