CamTHP*OH: a camphor-derived delta-lactol auxiliary for the effective desymmetrization of attached glycinamide residues. Asymmetric synthesis of alpha-amino carbonyl compounds.

Journal article

Stereoselective allylation of camphor and subsequent terminal hydroformylation affords a new delta-lactol auxiliary (camTHP*OH) on multigram scale. Stereoselective condensation with glycine dimethylamide and Cbz protection affords a camTHP*-desymmetrized glycinamide building block which undergoes efficient and highly diastereoselective metal enolate alkylation reactions. Acid-mediated deprotection affords the N-Cbz-protected alpha-amino amide products which may be converted directly to alpha-amino ketones on treatment with Grignard or organolithium reagents without loss of stereochemical integrity. [reaction: see text]

Authors: Dixon, D; Horan, R; Monck, N

• Publication status: Published
• Journal: Organic letters
• Volume: 6
• Issue: 24
• Pages: 4423-4426
• Publication date: 2004-11-01
• DOI: 10.1021/ol048569i
• EISSN: 1523-7052
• ISSN: 1523-7060
• Language: English