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Titanium-catalyzed enantioselective additions of alkyl groups to aldehydes: mechanistic studies and new concepts in asymmetric catalysis.
Acc Chem Res. 2003 Oct; 36(10):739-49.AC

Abstract

The catalytic asymmetric addition of alkyl groups to aldehydes is an important reaction in the enantioselective synthesis of secondary alcohols. This reaction can be catalyzed by zinc- or titanium-based catalysts. While the mechanism of the zinc/amino alcohol catalysts has received significant attention, the titanium-based catalysts have been less studied. This Account summarizes our mechanistic studies with bis(sulfonamide) and BINOL-derived titanium catalysts. It also describes our use of this reaction in the development of new approaches to asymmetric catalysis, including applications of diastereomeric catalysts and optimization of asymmetric catalysts with achiral and meso ligands.

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Authors+Show Affiliations

Walsh PJ
University of Pennsylvania, Department of Chemistry, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323. pwalsh@sas.upenn.edu

MeSH

AlcoholsAldehydesAlkylationCatalysisLigandsModels, ChemicalMolecular StructureNaphtholsOrganometallic CompoundsStereoisomerismSulfonamidesTitaniumZinc

Pub Type(s)

Journal Article
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.
Review

Language

eng

PubMed ID

14567707

Citation

Walsh, Patrick J.. "Titanium-catalyzed Enantioselective Additions of Alkyl Groups to Aldehydes: Mechanistic Studies and New Concepts in Asymmetric Catalysis." Accounts of Chemical Research, vol. 36, no. 10, 2003, pp. 739-49.
Walsh PJ. Titanium-catalyzed enantioselective additions of alkyl groups to aldehydes: mechanistic studies and new concepts in asymmetric catalysis. Acc Chem Res. 2003;36(10):739-49.
Walsh, P. J. (2003). Titanium-catalyzed enantioselective additions of alkyl groups to aldehydes: mechanistic studies and new concepts in asymmetric catalysis. Accounts of Chemical Research, 36(10), 739-49.
Walsh PJ. Titanium-catalyzed Enantioselective Additions of Alkyl Groups to Aldehydes: Mechanistic Studies and New Concepts in Asymmetric Catalysis. Acc Chem Res. 2003;36(10):739-49. PubMed PMID: 14567707.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Titanium-catalyzed enantioselective additions of alkyl groups to aldehydes: mechanistic studies and new concepts in asymmetric catalysis. A1 - Walsh,Patrick J, PY - 2003/10/22/pubmed PY - 2003/12/12/medline PY - 2003/10/22/entrez SP - 739 EP - 49 JF - Accounts of chemical research JO - Acc Chem Res VL - 36 IS - 10 N2 - The catalytic asymmetric addition of alkyl groups to aldehydes is an important reaction in the enantioselective synthesis of secondary alcohols. This reaction can be catalyzed by zinc- or titanium-based catalysts. While the mechanism of the zinc/amino alcohol catalysts has received significant attention, the titanium-based catalysts have been less studied. This Account summarizes our mechanistic studies with bis(sulfonamide) and BINOL-derived titanium catalysts. It also describes our use of this reaction in the development of new approaches to asymmetric catalysis, including applications of diastereomeric catalysts and optimization of asymmetric catalysts with achiral and meso ligands. SN - 0001-4842 UR - https://www.unboundmedicine.com/medline/citation/14567707/Titanium_catalyzed_enantioselective_additions_of_alkyl_groups_to_aldehydes:_mechanistic_studies_and_new_concepts_in_asymmetric_catalysis_ L2 - https://doi.org/10.1021/ar0300219 DB - PRIME DP - Unbound Medicine ER -