Asymmetric construction of quaternary carbon stereocenters: high stereoselection in Mukaiyama aldol reactions of 2-siloxyindoles with chiral aldehydes.Org Lett. 2005 Jun 23; 7(13):2795-7.OL
Abstract
[reaction: see text] A new synthesis of enantiopure 3,3-disubstituted oxindoles by stereoselective Mukaiyama aldol reaction of 3-substituted 2-siloxyindoles and chiral, enantiopure aldehydes having nitrogen or oxygen substituents at the alpha carbon is described. When the C3 substituent of the prochiral nucleophile is aryl or heteroaryl, stereoselectivity is high (10-80:1).
Links
MeSH
Pub Type(s)
Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, P.H.S.
Language
eng
PubMed ID
15957949
Citation
Adhikari, Susanta, et al. "Asymmetric Construction of Quaternary Carbon Stereocenters: High Stereoselection in Mukaiyama Aldol Reactions of 2-siloxyindoles With Chiral Aldehydes." Organic Letters, vol. 7, no. 13, 2005, pp. 2795-7.
Adhikari S, Caille S, Hanbauer M, et al. Asymmetric construction of quaternary carbon stereocenters: high stereoselection in Mukaiyama aldol reactions of 2-siloxyindoles with chiral aldehydes. Org Lett. 2005;7(13):2795-7.
Adhikari, S., Caille, S., Hanbauer, M., Ngo, V. X., & Overman, L. E. (2005). Asymmetric construction of quaternary carbon stereocenters: high stereoselection in Mukaiyama aldol reactions of 2-siloxyindoles with chiral aldehydes. Organic Letters, 7(13), 2795-7.
Adhikari S, et al. Asymmetric Construction of Quaternary Carbon Stereocenters: High Stereoselection in Mukaiyama Aldol Reactions of 2-siloxyindoles With Chiral Aldehydes. Org Lett. 2005 Jun 23;7(13):2795-7. PubMed PMID: 15957949.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Asymmetric construction of quaternary carbon stereocenters: high stereoselection in Mukaiyama aldol reactions of 2-siloxyindoles with chiral aldehydes.
AU - Adhikari,Susanta,
AU - Caille,Sebastien,
AU - Hanbauer,Martin,
AU - Ngo,Vinh X,
AU - Overman,Larry E,
PY - 2005/6/17/pubmed
PY - 2006/4/18/medline
PY - 2005/6/17/entrez
SP - 2795
EP - 7
JF - Organic letters
JO - Org Lett
VL - 7
IS - 13
N2 - [reaction: see text] A new synthesis of enantiopure 3,3-disubstituted oxindoles by stereoselective Mukaiyama aldol reaction of 3-substituted 2-siloxyindoles and chiral, enantiopure aldehydes having nitrogen or oxygen substituents at the alpha carbon is described. When the C3 substituent of the prochiral nucleophile is aryl or heteroaryl, stereoselectivity is high (10-80:1).
SN - 1523-7060
UR - https://www.unboundmedicine.com/medline/citation/15957949/Asymmetric_construction_of_quaternary_carbon_stereocenters:_high_stereoselection_in_Mukaiyama_aldol_reactions_of_2_siloxyindoles_with_chiral_aldehydes_
L2 - https://doi.org/10.1021/ol051172+
DB - PRIME
DP - Unbound Medicine
ER -