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Practical synthesis of chiral vinylphosphine oxides by direct nucleophilic substitution. Stereodivergent synthesis of aminophosphine ligands

Practical synthesis of chiral vinylphosphine oxides by direct nucleophilic substitution. Stereodivergent synthesis of aminophosphine ligands
Practical synthesis of chiral vinylphosphine oxides by direct nucleophilic substitution. Stereodivergent synthesis of aminophosphine ligands
A practical synthesis of optically pure alkylphenylvinylphosphine oxides is described, utilizing a nucleophilic displacement at phosphorus to install the vinyl moiety. The products were used to prepare classes of P-stereogenic aminophosphine (PN) and aminohydroxyphosphine (PNO) ligands. Stereocontrol can be exerted at various stages of the synthesis, to provide specific combinations of chirality in the final product. The effect of the stereogenic phosphorus and match-mismatch of chiralities of PNO ligands were examined in the asymmetric ruthenium-catalyzed hydrogen transfer reduction of three aryl ketones.
0022-3263
2472-2479
Oliana, M.
d67d3df1-430d-4ce6-bd21-820c281a13ad
King, F.
b3546275-e305-4f8a-9de2-1b6979a68c1c
Horton, P.N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Hursthouse, M.B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Hii, K.K.
5045523b-d83e-417d-a2be-c367cf908291
Oliana, M.
d67d3df1-430d-4ce6-bd21-820c281a13ad
King, F.
b3546275-e305-4f8a-9de2-1b6979a68c1c
Horton, P.N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Hursthouse, M.B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Hii, K.K.
5045523b-d83e-417d-a2be-c367cf908291

Oliana, M., King, F., Horton, P.N., Hursthouse, M.B. and Hii, K.K. (2006) Practical synthesis of chiral vinylphosphine oxides by direct nucleophilic substitution. Stereodivergent synthesis of aminophosphine ligands. Journal of Organic Chemistry, 71 (6), 2472-2479. (doi:10.1021/jo052575q).

Record type: Article

Abstract

A practical synthesis of optically pure alkylphenylvinylphosphine oxides is described, utilizing a nucleophilic displacement at phosphorus to install the vinyl moiety. The products were used to prepare classes of P-stereogenic aminophosphine (PN) and aminohydroxyphosphine (PNO) ligands. Stereocontrol can be exerted at various stages of the synthesis, to provide specific combinations of chirality in the final product. The effect of the stereogenic phosphorus and match-mismatch of chiralities of PNO ligands were examined in the asymmetric ruthenium-catalyzed hydrogen transfer reduction of three aryl ketones.

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Published date: 2006

Identifiers

Local EPrints ID: 44514
URI: http://eprints.soton.ac.uk/id/eprint/44514
ISSN: 0022-3263
PURE UUID: ad04f863-934d-46a3-b155-ea63e366118f
ORCID for P.N. Horton: ORCID iD orcid.org/0000-0001-8886-2016

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Date deposited: 05 Mar 2007
Last modified: 26 Nov 2019 01:53

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