Synthesis of new cyclopentane phosphine oxides

被引：2

作者：

Camps, Pelayo ^{[1
]}

Colet, Gisela ^{[1
]}

Segura, Sergi ^{[1
]}

Vazquez, Santiago ^{[1
]}

机构：

[1] Univ Barcelona, Fac Farm, Quim Farmaceut Lab, CSIC, Av Diagonal 643, E-08028 Barcelona, Spain

来源：

ARKIVOC | 2007年

关键词：

phosphine oxides; stereoselective epoxidation; Caglioti reaction; DFT calculations; GIAO; nucleophilic epoxide opening;

D O I：

10.3998/ark.5550190.0008.402

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(1r, 2t, 5t)- 2- Diphenylphosphinoyl- 5-[( diphenylphosphinoyl) methyl] cyclopentanol (10) was prepared in good yield from 3-methoxy-2-cyclopentenone by a five-step sequence which takes advantage of the electrophilic character of positions 1 and 3 of the starting material.

引用

页码：8 / 19

页数：12

共 42 条

[1] A CONVENIENT PREPARATION OF ACETONE SOLUTIONS OF DIMETHYLDIOXIRANE [J].

ADAM, W ;

BIALAS, J ;

HADJIARAPOGLOU, L .

CHEMISCHE BERICHTE, 1991, 124 (10) :2377-2377

[2] DFT calculation of NMR JFF spin-spin coupling constants in fluorinated pyridines [J].

Barone, V ;

Peralta, JE ;

Contreras, RH ;

Snyder, JP .

JOURNAL OF PHYSICAL CHEMISTRY A, 2002, 106 (23) :5607-5612

[3] PREPARATION AND CONFORMATION OF (E,E)-1,5-CYCLOOCTADIENE [J].

BOECKH, D ;

HUISGEN, R ;

NOTH, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (04) :1248-1249

[4] ENANTIOSELECTIVE CATALYSIS .42. SYNTHESIS OF OPTICALLY-ACTIVE PHOSPHANES VIA SHARPLESS EPOXIDATION [J].

BRUNNER, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (05) :718-719

[5] REACTION OF TOSYLHYDRAZONES WITH LITHIUM ALUMINIUM HYDRIDE [J].

CAGLIOTI, L ;

MAGI, M .

TETRAHEDRON, 1963, 19 (07) :1127-&

[6] Easy access to cis-1,3-disubstituted cyclopentane 1,4-diphosphines [J].

Camps, P ;

Colet, G ;

Vázquez, S .

ARKIVOC, 2003, :16-23

[7] Towards chiral non-racemic cis-1,3-disubstituted cyclopentane 1,4-diphosphines [J].

Camps, P ;

Colet, G ;

Font-Bardia, M ;

Muñoz-Torrero, V ;

Solans, X ;

Vázquez, S .

TETRAHEDRON-ASYMMETRY, 2002, 13 (07) :759-778

[8] Straightforward regio- and stereo-selective synthesis of t-2-[(diphenylphosphinoyl)methyl]-c-3-(disubstitutedphosphinoyl)-r-1-cyclopentanols [J].

Camps, P ;

Colet, G ;

Font-Bardia, M ;

Muñoz-Torrero, V ;

Solans, X ;

Vázquez, S .

TETRAHEDRON, 2002, 58 (18) :3473-3484

[9] A comparison of models for calculating nuclear magnetic resonance shielding tensors [J].

Cheeseman, JR ;

Trucks, GW ;

Keith, TA ;

Frisch, MJ .

JOURNAL OF CHEMICAL PHYSICS, 1996, 104 (14) :5497-5509

[10] ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION OF ALLYLIC PHOSPHINE OXIDES [J].

CLAYDEN, J ;

WARREN, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (19) :2811-2823

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