Organocatalytic asymmetric aldol reaction of hydroxyacetone with β,γ-unsaturated α-keto esters: facile access to chiral tertiary alcohols.Org Lett. 2011 Oct 07; 13(19):5248-51.OL
Abstract
An efficient direct asymmetric aldol reaction between hydroxyacetone and β,γ-unsaturated α-keto esters has been successfully developed. In the presence of 9-amino-9-deoxy-epi-cinchonine and trifluoroacetic acid, the direct aldol reaction of O-protected hydroxyacetone proceeded in a highly enantioselective manner, affording the desired adducts containing a chiral tertiary alcohol in high yields and with excellent enantioselectivities. The aldol products obtained are valuable precursors for the synthesis of 2-substituted glycerol derivatives.
Links
Pub Type(s)
Journal Article
Research Support, Non-U.S. Gov't
Language
eng
PubMed ID
21902199
Citation
Liu, Chen, et al. "Organocatalytic Asymmetric Aldol Reaction of Hydroxyacetone With Β,γ-unsaturated Α-keto Esters: Facile Access to Chiral Tertiary Alcohols." Organic Letters, vol. 13, no. 19, 2011, pp. 5248-51.
Liu C, Dou X, Lu Y. Organocatalytic asymmetric aldol reaction of hydroxyacetone with β,γ-unsaturated α-keto esters: facile access to chiral tertiary alcohols. Org Lett. 2011;13(19):5248-51.
Liu, C., Dou, X., & Lu, Y. (2011). Organocatalytic asymmetric aldol reaction of hydroxyacetone with β,γ-unsaturated α-keto esters: facile access to chiral tertiary alcohols. Organic Letters, 13(19), 5248-51. https://doi.org/10.1021/ol2021274
Liu C, Dou X, Lu Y. Organocatalytic Asymmetric Aldol Reaction of Hydroxyacetone With Β,γ-unsaturated Α-keto Esters: Facile Access to Chiral Tertiary Alcohols. Org Lett. 2011 Oct 7;13(19):5248-51. PubMed PMID: 21902199.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Organocatalytic asymmetric aldol reaction of hydroxyacetone with β,γ-unsaturated α-keto esters: facile access to chiral tertiary alcohols.
AU - Liu,Chen,
AU - Dou,Xiaowei,
AU - Lu,Yixin,
Y1 - 2011/09/08/
PY - 2011/9/10/entrez
PY - 2011/9/10/pubmed
PY - 2012/1/18/medline
SP - 5248
EP - 51
JF - Organic letters
JO - Org Lett
VL - 13
IS - 19
N2 - An efficient direct asymmetric aldol reaction between hydroxyacetone and β,γ-unsaturated α-keto esters has been successfully developed. In the presence of 9-amino-9-deoxy-epi-cinchonine and trifluoroacetic acid, the direct aldol reaction of O-protected hydroxyacetone proceeded in a highly enantioselective manner, affording the desired adducts containing a chiral tertiary alcohol in high yields and with excellent enantioselectivities. The aldol products obtained are valuable precursors for the synthesis of 2-substituted glycerol derivatives.
SN - 1523-7052
UR - https://www.unboundmedicine.com/medline/citation/21902199/Organocatalytic_asymmetric_aldol_reaction_of_hydroxyacetone_with_βγ_unsaturated_α_keto_esters:_facile_access_to_chiral_tertiary_alcohols_
L2 - https://doi.org/10.1021/ol2021274
DB - PRIME
DP - Unbound Medicine
ER -
