Highly enantioselective hetero-Diels-Alder reaction of brassard diene with aromatic aldehydes

被引：74

作者：

Fan, Q ^{[1
]}

Lin, LL

Liu, J

Huang, YZ

Feng, XM

Zhang, GL

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

[2] Chinese Acad Sci, Chengdu Inst Biol, Chengdu, Peoples R China

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 13期

关键词：

D O I：

10.1021/ol049364c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hetero-Diels-Alder reactions of Brassard diene with aromatic aldehydes were carried out smoothly in the presence of titanium(IV) tridentate Schiff base complexes to give the corresponding chiral delta-lactones in high enantioselectivities (up to 99% ee) under mild conditions.

引用

收藏

页码：2185 / 2188

页数：4

相关论文

共 58 条

[1] cis-stilbene and (1α,2β,3α)-(2-ethenyl-3-methoxycyclopropyl)benzene as mechanistic probes in the MnIII(salen)-catalyzed epoxidation:: Influence of the oxygen source and the counterion on the diastereoselectivity of the competitive concerted and radical-type oxygen transfer [J].

Adam, W ;

Roschmann, KJ ;

Saha-Möller, CR ;

Seebach, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (18) :5068-5073

[2] A novel catalytic and highly enantioselective approach for the synthesis of optically active carbohydrate derivatives [J].

Audrain, H ;

Thorhauge, J ;

Hazell, RG ;

Jorgensen, KA .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15) :4487-4497

[3] A new catalytic enantioselective approach to optically active lactones by addition reactions to α-dicarbonyl compounds [J].

Audrain, H ;

Jorgensen, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (46) :11543-11544

[4] METABOLIC PRODUCTS OF MICROORGANISMS .265. PRELACTONE-C AND PRELACTONE-B, OLIGOKETIDES FROM STREPTOMYCES PRODUCING CONCANAMYCINS AND BAFILOMYCINS [J].

BINDSEIL, KU ;

ZEECK, A .

HELVETICA CHIMICA ACTA, 1993, 76 (01) :150-157

[5] 5,6-dihydropyran-2-ones possessing various sulfonyl functionalities: Potent nonpeptidic inhibitors of HIV protease [J].

Boyer, FE ;

Prasad, JVNV ;

Domagala, JM ;

Ellsworth, EL ;

Gajda, C ;

Hagen, SE ;

Markoski, LJ ;

Tait, BD ;

Lunney, EA ;

Palovsky, A ;

Ferguson, D ;

Graham, N ;

Holler, T ;

Hupe, D ;

Nouhan, C ;

Tummino, PJ ;

Urumov, A ;

Zeikus, E ;

Zeikus, G ;

Gracheck, SJ ;

Sanders, JM ;

VanderRoest, S ;

Brodfuehrer, J ;

Iyer, K ;

Sinz, M ;

Gulnik, SV ;

Erickson, JW .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (05) :843-858

[6] Synthesis of (+)-prelactone B [J].

Chakraborty, TK ;

Tapadar, S .

TETRAHEDRON LETTERS, 2003, 44 (12) :2541-2543

[7] Catalyst-controlled inverse-electron-demand hetero-Diels-Alder reactions in the enantio- and diastereloselective synthesis of iridoid natural products [J].

Chavez, DE ;

Jacobsen, EN .

ORGANIC LETTERS, 2003, 5 (14) :2563-2565

[8] Catalytic asymmetric oxidation of tert-butyl disulfide.: Synthesis of tert-butanesulfinamides, tert-butyl sulfoxides, and tert-butanesulfinimines [J].

Cogan, DA ;

Liu, GC ;

Kim, KJ ;

Backes, BJ ;

Ellman, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (32) :8011-8019

[9]

Corey EJ, 2002, ANGEW CHEM INT EDIT, V41, P1650, DOI 10.1002/1521-3773(20020517)41:10<1650::AID-ANIE1650>3.0.CO

[10]

2-B

← 1 2 3 4 5 6 →