A Highly Regioselective Ring-Opening Metathesis-Cross Metathesis Process Modulated by the Electronic Effects of the Cross Metathesis Partner: An Entry to Quaternary Prolines

被引：11

作者：

Carreras, Javier ^{[1
]}

Avenoza, Alberto ^{[1
]}

Busto, Jesus H. ^{[1
]}

Peregrina, Jesus M. ^{[1
]}

机构：

[1] Univ La Rioja, Dept Quim, UA CSIC, Grp Sintesis Quim La Rioja, Logrono 26006, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 04期

关键词：

ALPHA-AMINO-ACIDS; OLEFIN-METATHESIS; STEREOSELECTIVE-SYNTHESIS; NORBORNENE DERIVATIVES; ASYMMETRIC-SYNTHESIS; CLOSING METATHESIS; SUBSTITUENTS; COMPLEXES; CATALYSTS; ABH;

D O I：

10.1021/jo802399k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A modulation of the regioselectivity in the ring-opening metathesis-cross metathesis (ROCM) process, originated by the electronic features of the acyclic olefin, is described. Electron-poor and electron-rich olefins showed opposing behavior giving different regioisomers. The reaction opens the way to the synthesis of interesting proline analogues incorporating a quaternary stereocenter.

引用

页码：1736 / 1739

页数：4

共 56 条

[11] Regioselective ring-opening metathesis-cross metathesis of bridgehead-substituted 7-azanorbornene [J].

Carreras, J. ;

Avenoza, A. ;

Busto, J. H. ;

Peregrina, J. M. .

ORGANIC LETTERS, 2007, 9 (07) :1235-1238

[12] Stereoselective synthesis of quaternary α-amino acids.: Part 2.: Cyclic compounds [J].

Cativiela, C ;

Díaz-de-Villegas, MD .

TETRAHEDRON-ASYMMETRY, 2000, 11 (03) :645-732

[13] Recent progress on the stereoselective synthesis of acyclic quaternary α-amino acids [J].

Cativiela, Carlos ;

Diaz-de-Villegas, Maria D. .

TETRAHEDRON-ASYMMETRY, 2007, 18 (05) :569-623

[14] Olefin metathesis: The early days (Nobel lecture) [J].

Chauvin, Y .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (23) :3740-3747

[15] Comparison of Ru- and Mo-based chiral olefin metathesis catalysts. Complementarity in asymmetric ring-opening/cross-metathesis reactions of oxa- and azabicycles [J].

Cortez, G. Alex ;

Baxter, Carl A. ;

Schrock, Richard R. ;

Hoveyda, Amir H. .

ORGANIC LETTERS, 2007, 9 (15) :2871-2874

[16] Efficient enantioselective synthesis of piperidines through catalytic asymmetric ring-opening/cross-metathesis reactions [J].

Cortez, G. Alex ;

Schrock, Richard R. ;

Hoveyda, Amir H. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (24) :4534-4538

[17] Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis [J].

Deiters, A ;

Martin, SF .

CHEMICAL REVIEWS, 2004, 104 (05) :2199-2238

[18] Ring-opening cross metathesis of 1,3-cyclopentadiene-heterodienophile cycloadducts to produce cyclic hydrazines and hydroxylamines [J].

Ellis, JM ;

King, SB .

TETRAHEDRON LETTERS, 2002, 43 (33) :5833-5835

[19] Recent advances in the total synthesis of piperidine and pyrrolidine natural alkaloids with ring-closing metathesis as a key step [J].

Felpin, FX ;

Lebreton, J .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (19) :3693-3712

[20]

Feng J, 2002, EUR J ORG CHEM, V2002, P2942

← 1 2 3 4 5 6 →