The Baylis-Hillman reaction with chiral α-amino aldehydes under racemization-free conditions

被引：28

作者：

Coelho, F

Diaz, G

Abella, CAM

Almeida, WP

机构：

[1] Univ Estadual Campinas, Lab Synth Nat Prod & Drugs, DQO, IQ, BR-13084971 Campinas, SP, Brazil

[2] Unioeste, Lab Organ Synth & Nat Prod, BR-85900970 Toledo, PR, Brazil

[3] Univ Estadual Campinas, Inst Biol, Grad Program Cellular & Struct Biol, BR-13083970 Campinas, SP, Brazil

来源：

SYNLETT | 2006年 / 03期

关键词：

aldehydes; amino aldehydes; alkaloids; ring closure; stereoselectivity;

D O I：

10.1055/s-2006-926239

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Baylis-Hillman reaction with chiral a-amino aldehydes has been revisited. The reaction carried out under the influence of ultrasound avoids the aldehyde racemization almost completely, providing useful chiral substrates which can be used as starting materials for the synthesis of natural products. To demonstrate the synthetic applicability of these adducts, the easy preparation of a bicyclic lactam with an indolizidinic skeleton was accomplished.

引用

收藏

页码：435 / 439

页数：5

相关论文

共 49 条

[1] Reevaluation of the mechanism of the Baylis-Hillman reaction: Implications for asymmetric catalysis [J].

Aggarwal, VK ;

Fulford, SY ;

Lloyd-Jones, GC .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (11) :1706-1708

[2]

Ahn N. T., 1980, TOP CURR CHEM, V88, P144

[3] Straightforward asymmetric entry to highly functionalized 3-substituted 3-hydroxy-β-lactams via Baylis-Hillman or bromoallylation reactions [J].

Alcaide, B ;

Almendros, P ;

Aragoncillo, C ;

Rodríguez-Acebes, R .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (03) :826-831

[4] Straightforward asymmetric entry to highly functionalized medium-sized rings fused to β-lactams via chemo- and stereocontrolled divergent radical cyclization of Baylis-Hillman adducts derived from 4-oxoazetidine-2-carbaldehydes [J].

Alcaide, B ;

Almendros, P ;

Aragoncillo, C .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (05) :1612-1620

[5] An easy and stereoselective synthesis of N-Boc-dolaproine via the Baylis-Hillman reaction [J].

Almeida, WP ;

Coelho, F .

TETRAHEDRON LETTERS, 2003, 44 (05) :937-940

[6]

AMEER F, 1986, S AFR J CHEM, V39, P57

[7] The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction [J].

Basavaiah, D ;

Rao, PD ;

Hyma, RS .

TETRAHEDRON, 1996, 52 (24) :8001-8062

[8] Recent advances in the Baylis-Hillman reaction and applications [J].

Basavaiah, D ;

Rao, AJ ;

Satyanarayana, T .

CHEMICAL REVIEWS, 2003, 103 (03) :811-891

[9] Versatile and stereoselective synthesis of diamino diol dipeptide isosteres, core units of pseudopeptide HIV protease inhibitors [J].

Benedetti, F ;

Miertus, S ;

Norbedo, S ;

Tossi, A ;

Zlatoidzky, P .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26) :9348-9353

[10]

Bodanszky M., 1994, The Practice of Peptide Synthesis, V2nd

← 1 2 3 4 5 →