Stereoselective cyclization and pyramidal inversion strategies for P-chirogenic phospholane synthesis.
作者： Garrett Hoge
DOI: 10.1021/JA048079L
关键词: Rhodium 、 Stereochemistry 、 Enantioselective synthesis 、 Oxidative coupling of methane 、 Asymmetric hydrogenation 、 Chemistry 、 Organic synthesis 、 Catalysis 、 Stereoselectivity
摘要: Preparation of P-chirogenic mono- and bisphospholanes is reported. The demonstrated method employs a stereoselective cyclization cyclic sulfates with primary phosphines in the presence base to generate "cis" or "cis/cis" phospholanes followed by heat-induced pyramidal inversion provide "trans" "trans/trans" phospholanes. A rhodium complex one phospholane applied highly enantioselective asymmetric hydrogenation substrate precursor pharmaceutical candidate pregabalin.
acs.org
unirioja.es
sci-hub.se 参考文章(11)
Hideo Nemoto, Mitsuo Nagai, Keiichiro Fukumoto, Tetsuji Kametani, Synthetic approach to (+)-aldosterone and its relatives. 1. Synthesis of (+)-trans-4,5-(4-methoxybenzo)-1.beta.,7a.beta.-[2.alpha.-(methoxymethyl)-5-oxofuro]hydrindan Journal of Organic Chemistry. ,vol. 50, pp. 2764- 2766 ,(1985) , 10.1021/JO00215A034
Aaron L. Bluhm, Julius. Weinstein, Stable radicals by photooxidation of nitrones Journal of the American Chemical Society. ,vol. 92, pp. 1444- 1445 ,(1970) , 10.1021/JA00708A078
Uzi Ravid, Robert M. Silverstein, Leverett R. Smith, Synthesis of the enantiomers of 4-substituted γ-lactones with known absolute configuration Tetrahedron. ,vol. 34, pp. 1449- 1452 ,(1978) , 10.1016/0040-4020(78)80164-1
Yoshinori Yamanoi, Tsuneo Imamoto, Methylene-Bridged P-Chiral Diphosphines in Highly Enantioselective Reactions The Journal of Organic Chemistry. ,vol. 64, pp. 2988- 2989 ,(1999) , 10.1021/JO990131M
Herbert Hommer, Barbara Gordillo, Synthesis and Study of the Thermal Epimerization of r -2-Ethoxy- cis -4- cis -5-Dimethyl-1,3,2-λ 3 -Dioxaphospholane Using 31 P NMR Phosphorus Sulfur and Silicon and The Related Elements. ,vol. 177, pp. 465- 470 ,(2002) , 10.1080/10426500210245
Michael Reggelin, Melanie Schultz, Michael Holbach, Helical Chiral Polymers without Additional Stereogenic Units: A New Class of Ligands in Asymmetric Catalysis Angewandte Chemie International Edition. ,vol. 41, pp. 1614- 1617 ,(2002) , 10.1002/1521-3773(20020503)41:9<1614::AID-ANIE1614>3.0.CO;2-5
Wenjun Tang, Xumu Zhang, A Chiral 1,2-Bisphospholane Ligand with a Novel Structural Motif: Applications in Highly Enantioselective Rh-Catalyzed Hydrogenations Angewandte Chemie International Edition. ,vol. 41, pp. 1612- 1614 ,(2002) , 10.1002/1521-3773(20020503)41:9<1612::AID-ANIE1612>3.0.CO;2-H
Atsushi Ohashi, Tsuneo Imamoto, Highly Enantioselective Hydrogenation of α-Dehydroamino Acids by Rhodium Complexes with New Unsymmetric P−Chirogenic Bisphosphine Ligands Organic Letters. ,vol. 3, pp. 373- 375 ,(2001) , 10.1021/OL006876S
Garrett Hoge, Synthesis of both enantiomers of a P-chirogenic 1,2-bisphospholanoethane ligand via convergent routes and application to rhodium-catalyzed asymmetric hydrogenation of CI-1008 (pregabalin). Journal of the American Chemical Society. ,vol. 125, pp. 10219- 10227 ,(2003) , 10.1021/JA034715O
Chang S. Hsu, Donald Cox, Michael L. Gross, Kenneth A. Caldwell, Daryl E. Giblin, Endohedral complexes of fullerene radical cations Journal of the American Chemical Society. ,vol. 113, pp. 8519- 8521 ,(1991) , 10.1021/JA00022A048