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

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Leroy, Bernard Marko, Istvan [UCL]

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.

Document type Article de périodique (Journal article) – Journal Article
Access type Accès restreint
Publication date 2002
Language Anglais
Journal information "The Journal of organic chemistry" - Vol. 67, no. 25, p. 8744-52 (2002)
Peer reviewed yes
issn 0022-3263
Publication status Publié
Affiliation UCL - SC/CHIM - Département de chimie
Links
Bibliographic reference Leroy, Bernard ; Marko, Istvan. Connective synthesis of polysubstituted tetrahydropyrans by a novel and stereocontrolled metallo-ene/Intramolecular Sakurai Cyclization sequence.. In: The Journal of organic chemistry, Vol. 67, no. 25, p. 8744-52 (2002)
Permanent URL http://hdl.handle.net/2078.1/9323