Michael reactions of titanium enolates of glycolic acid derivatives with the Weinreb and morpholine amides of acrylic acid

被引：19

作者：

Olivella, Anna ^{[1
]}

Rodriguez-Escrich, Carles ^{[1
]}

Urpi, Felix ^{[1
]}

Vilarrasa, Jaume ^{[1
]}

机构：

[1] Univ Barcelona, Fac Quim, Dept Quim Organ, E-08028 Barcelona, Catalonia, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 04期

关键词：

D O I：

10.1021/jo702240n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The conjugate additions of titanium enolates of glycolate-derived chiral oxazolidin-2-ones to various Michael acceptors have been evaluated as an entry to enantiopure 1,2,5-trioxygenated and related synthons. alpha,beta-unsaturated Weinreb and morpholine amides do react under suitable conditions and their adducts can be converted to diverse C1-C5 chiral fragments.

引用

页码：1578 / 1581

页数：4

共 32 条

[1] Synthesis of (-)-amphidinolide K fragment C9-C22 [J].

Andreou, T ;

Costa, AM ;

Esteban, L ;

Gonzàlez, L ;

Mas, G ;

Vilarrasa, J .

ORGANIC LETTERS, 2005, 7 (19) :4083-4086

[2] Addition of organocerium reagents to morpholine amides:: Synthesis of important pheromone components of Achaea janata [J].

Badioli, M ;

Ballini, R ;

Bartolacci, M ;

Bosica, G ;

Torregiani, E ;

Marcantoni, E .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25) :8938-8942

[3]

Brenner M, 1999, HELV CHIM ACTA, V82, P2365, DOI 10.1002/(SICI)1522-2675(19991215)82:12<2365::AID-HLCA2365>3.0.CO

[4]

2-#

[5] SuperQuat N-acyl-5,5-dimethyloxazolidin-2-ones for the asymmetric synthesis of α-alkyl and β-alkyl aldehydes [J].

Bull, SD ;

Davies, SG ;

Nicholson, RL ;

Sanganee, HJ ;

Smith, AD .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (16) :2886-2899

[6] SuperQuat, (S)-4-benzyl-5,5-dimethyl-oxazolidin-2-one for the asymmetric synthesis of α-substituted aldehydes [J].

Bull, SD ;

Davies, SG ;

Nicholson, RL ;

Sanganee, HJ ;

Smith, AD .

TETRAHEDRON-ASYMMETRY, 2000, 11 (17) :3475-3479

[7] Efficient synthesis of acylsilanes using morpholine amides [J].

Clark, CT ;

Milgram, BC ;

Scheidt, KA .

ORGANIC LETTERS, 2004, 6 (22) :3977-3980

[8] Stereospecific cyclopropanation of highly substituted C-C double bonds promoted by CrCl2.: Stereoselective synthesis of cyclopropanecarboxamides and cyclopropyl ketones [J].

Concellon, Jose M. ;

Rodriguez-Solla, Humberto ;

Mejica, Carmen ;

Blanco, Elena G. .

ORGANIC LETTERS, 2007, 9 (16) :2981-2984

[9] N-alkoxyacrylamides as substrates for enantioselective Diels-Alder reactions [J].

Corminboeuf, O ;

Renaud, P .

ORGANIC LETTERS, 2002, 4 (10) :1735-1738

[10] Diastereoselective alkylations of oxazolidinone glycolates: A useful extension of the Evans asymmetric alkylation [J].

Crimmins, MT ;

Emmitte, KA ;

Katz, JD .

ORGANIC LETTERS, 2000, 2 (14) :2165-2167

← 1 2 3 4 →