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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).

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Authors+Show Affiliations

Adhikari S
Department of Chemistry, 516 Rowland Hall, University of California, Irvine, California 92697-2025, USA.
Caille S
No affiliation info available
Hanbauer M
No affiliation info available
Ngo VX
No affiliation info available
Overman LE
No affiliation info available

MeSH

AldehydesIndole AlkaloidsIndolesMolecular StructureOrganometallic CompoundsSiliconStereoisomerism

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 -