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Lewis base-catalyzed conjugate reduction and reductive aldol reaction of alpha,beta-unsaturated ketones using trichlorosilane.
Chem Commun (Camb). 2008 Sep 28CC

Abstract

Lewis bases such as Ph3P=O and HMPA catalyze the 1,4-reduction of alpha,beta-unsaturated ketones with trichlorosilane, and because the 1,2-reduction of aldehydes scarcely proceeded under the conditions, one-pot reductive aldol reactions with aldehydes were successfully achieved; preliminary studies using a chiral Lewis base revealed a high potential for enantioselective catalysis.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Sugiura M
Faculty of Medical and Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto, 862-0973, Japan. msugiura@kumamoto-u.ac.jp
Sato N
No affiliation info available
Kotani S
No affiliation info available
Nakajima M
No affiliation info available

MeSH

AlcoholsAldehydesCatalysisHempaKetonesMolecular StructureOrganophosphorus CompoundsOxidation-ReductionSilanesStereoisomerism

Pub Type(s)

Journal Article

Language

eng

PubMed ID

18802553

Citation

Sugiura, Masaharu, et al. "Lewis Base-catalyzed Conjugate Reduction and Reductive Aldol Reaction of Alpha,beta-unsaturated Ketones Using Trichlorosilane." Chemical Communications (Cambridge, England), 2008, pp. 4309-11.
Sugiura M, Sato N, Kotani S, et al. Lewis base-catalyzed conjugate reduction and reductive aldol reaction of alpha,beta-unsaturated ketones using trichlorosilane. Chem Commun (Camb). 2008.
Sugiura, M., Sato, N., Kotani, S., & Nakajima, M. (2008). Lewis base-catalyzed conjugate reduction and reductive aldol reaction of alpha,beta-unsaturated ketones using trichlorosilane. Chemical Communications (Cambridge, England), (36), 4309-11. https://doi.org/10.1039/b807529h
Sugiura M, et al. Lewis Base-catalyzed Conjugate Reduction and Reductive Aldol Reaction of Alpha,beta-unsaturated Ketones Using Trichlorosilane. Chem Commun (Camb). 2008 Sep 28;(36)4309-11. PubMed PMID: 18802553.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Lewis base-catalyzed conjugate reduction and reductive aldol reaction of alpha,beta-unsaturated ketones using trichlorosilane. AU - Sugiura,Masaharu, AU - Sato,Norimasa, AU - Kotani,Shunsuke, AU - Nakajima,Makoto, Y1 - 2008/07/17/ PY - 2008/9/20/pubmed PY - 2008/12/23/medline PY - 2008/9/20/entrez SP - 4309 EP - 11 JF - Chemical communications (Cambridge, England) JO - Chem Commun (Camb) IS - 36 N2 - Lewis bases such as Ph3P=O and HMPA catalyze the 1,4-reduction of alpha,beta-unsaturated ketones with trichlorosilane, and because the 1,2-reduction of aldehydes scarcely proceeded under the conditions, one-pot reductive aldol reactions with aldehydes were successfully achieved; preliminary studies using a chiral Lewis base revealed a high potential for enantioselective catalysis. SN - 1359-7345 UR - https://www.unboundmedicine.com/medline/citation/18802553/Lewis_base_catalyzed_conjugate_reduction_and_reductive_aldol_reaction_of_alphabeta_unsaturated_ketones_using_trichlorosilane_ L2 - https://doi.org/10.1039/b807529h DB - PRIME DP - Unbound Medicine ER -