Alkylation of chiral alpha-hydroxy ketones derived from (1R)-(+)-camphor. An asymmetric variant of the classical acetylene route to carbonyl compounds

C Palomo; M Oiarbide; A Mielgo; A González; J M García; C Landa; A Lecumberri; A Linden

doi:10.1021/ol0163530

Alkylation of chiral alpha-hydroxy ketones derived from (1R)-(+)-camphor. An asymmetric variant of the classical acetylene route to carbonyl compounds

Org Lett. 2001 Oct 18;3(21):3249-52. doi: 10.1021/ol0163530.

Authors

C Palomo¹, M Oiarbide, A Mielgo, A González, J M García, C Landa, A Lecumberri, A Linden

Affiliation

¹ Departamento de Química Orgánica I, Facultad de Química, Universidad del País Vasco, Apdo. 1072, 20080-San Sebastián, Spain. qoppanic@sc.ehu.edu

PMID: 11594806
DOI: 10.1021/ol0163530

Abstract

[reaction: see text]. The asymmetric version of the traditional route for transforming acetylene into alpha-branched carbonyl compounds is now feasible for the first time. The method involves the temporary attachment of camphor to acetylene and gives a remarkably high diastereo- and enantioselectivity.