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.
Links
MeSH
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 -