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Enantioselective aldol reactions catalyzed by chiral phosphine oxides.
Chem Rec. 2013 Aug; 13(4):362-70.CR

Abstract

The development of enantioselective aldol reactions catalyzed by chiral phosphine oxides is described. The aldol reactions presented herein do not require the prior preparation of the masked enol ethers from carbonyl compounds as aldol donors. The reactions proceed through a trichlorosilyl enol ether intermediate, formed in situ from carbonyl compounds, which then acts as the aldol donor. Phosphine oxides activate the trichlorosilyl enol ethers to afford the aldol adducts with high stereoselectivities. This procedure was used to realize a directed cross-aldol reaction between ketones and two types of double aldol reactions (a reaction at one/two α position(s) of a carbonyl group) with high diastereo- and enantioselectivities.

Authors+Show Affiliations

Priority Organization for Innovation and Excellence, Kumamoto University, Kumamoto 862-0973, Japan.No affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

23828817

Citation

Kotani, Shunsuke, et al. "Enantioselective Aldol Reactions Catalyzed By Chiral Phosphine Oxides." Chemical Record (New York, N.Y.), vol. 13, no. 4, 2013, pp. 362-70.
Kotani S, Sugiura M, Nakajima M. Enantioselective aldol reactions catalyzed by chiral phosphine oxides. Chem Rec. 2013;13(4):362-70.
Kotani, S., Sugiura, M., & Nakajima, M. (2013). Enantioselective aldol reactions catalyzed by chiral phosphine oxides. Chemical Record (New York, N.Y.), 13(4), 362-70. https://doi.org/10.1002/tcr.201300004
Kotani S, Sugiura M, Nakajima M. Enantioselective Aldol Reactions Catalyzed By Chiral Phosphine Oxides. Chem Rec. 2013;13(4):362-70. PubMed PMID: 23828817.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective aldol reactions catalyzed by chiral phosphine oxides. AU - Kotani,Shunsuke, AU - Sugiura,Masaharu, AU - Nakajima,Makoto, Y1 - 2013/07/04/ PY - 2013/03/09/received PY - 2013/7/6/entrez PY - 2013/7/6/pubmed PY - 2014/2/15/medline KW - aldol reaction KW - diastereoselectivity KW - enantioselectivity KW - organocatalysis KW - phosphine oxides SP - 362 EP - 70 JF - Chemical record (New York, N.Y.) JO - Chem Rec VL - 13 IS - 4 N2 - The development of enantioselective aldol reactions catalyzed by chiral phosphine oxides is described. The aldol reactions presented herein do not require the prior preparation of the masked enol ethers from carbonyl compounds as aldol donors. The reactions proceed through a trichlorosilyl enol ether intermediate, formed in situ from carbonyl compounds, which then acts as the aldol donor. Phosphine oxides activate the trichlorosilyl enol ethers to afford the aldol adducts with high stereoselectivities. This procedure was used to realize a directed cross-aldol reaction between ketones and two types of double aldol reactions (a reaction at one/two α position(s) of a carbonyl group) with high diastereo- and enantioselectivities. SN - 1528-0691 UR - https://www.unboundmedicine.com/medline/citation/23828817/Enantioselective_aldol_reactions_catalyzed_by_chiral_phosphine_oxides_ L2 - https://doi.org/10.1002/tcr.201300004 DB - PRIME DP - Unbound Medicine ER -