CamTHP*OH: a camphor-derived delta-lactol auxiliary for the effective desymmetrization of attached glycinamide residues. Asymmetric synthesis of alpha-amino carbonyl compounds.Org Lett. 2004 Nov 25; 6(24):4423-6.OL
Abstract
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]
Pub Type(s)
Journal Article
Language
eng
PubMed ID
15548041
Citation
Dixon, Darren J., et al. "CamTHP*OH: a Camphor-derived Delta-lactol Auxiliary for the Effective Desymmetrization of Attached Glycinamide Residues. Asymmetric Synthesis of Alpha-amino Carbonyl Compounds." Organic Letters, vol. 6, no. 24, 2004, pp. 4423-6.
Dixon DJ, Horan RA, Monck NJ. CamTHP*OH: a camphor-derived delta-lactol auxiliary for the effective desymmetrization of attached glycinamide residues. Asymmetric synthesis of alpha-amino carbonyl compounds. Org Lett. 2004;6(24):4423-6.
Dixon, D. J., Horan, R. A., & Monck, N. J. (2004). CamTHP*OH: a camphor-derived delta-lactol auxiliary for the effective desymmetrization of attached glycinamide residues. Asymmetric synthesis of alpha-amino carbonyl compounds. Organic Letters, 6(24), 4423-6.
Dixon DJ, Horan RA, Monck NJ. CamTHP*OH: a Camphor-derived Delta-lactol Auxiliary for the Effective Desymmetrization of Attached Glycinamide Residues. Asymmetric Synthesis of Alpha-amino Carbonyl Compounds. Org Lett. 2004 Nov 25;6(24):4423-6. PubMed PMID: 15548041.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - CamTHP*OH: a camphor-derived delta-lactol auxiliary for the effective desymmetrization of attached glycinamide residues. Asymmetric synthesis of alpha-amino carbonyl compounds.
AU - Dixon,Darren J,
AU - Horan,Richard A J,
AU - Monck,Nathaniel J T,
PY - 2004/11/19/pubmed
PY - 2004/11/19/medline
PY - 2004/11/19/entrez
SP - 4423
EP - 6
JF - Organic letters
JO - Org Lett
VL - 6
IS - 24
N2 - 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]
SN - 1523-7060
UR - https://www.unboundmedicine.com/medline/citation/15548041/CamTHP_OH:_a_camphor_derived_delta_lactol_auxiliary_for_the_effective_desymmetrization_of_attached_glycinamide_residues__Asymmetric_synthesis_of_alpha_amino_carbonyl_compounds_
DB - PRIME
DP - Unbound Medicine
ER -
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