Enantioselective Diels-Alder reactions catalyzed by chiral 1,1′-(2,2′-bisacylamino)binaphthalene-ytterbium complex

被引：56

作者：

Nishida, A ^{[1
]}

Yamanaka, M ^{[1
]}

Nakagawa, M ^{[1
]}

机构：

[1] Chiba Univ, Fac Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 08期

关键词：

amides; asymmetric reactions; Diels-Alder reaction; lanthanides;

D O I：

10.1016/S0040-4039(98)02709-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new axially chiral ligand, 1,1'-(2,2'-bisacylamino)binaphthalene, was found to be effective in the ytterbium-catalyzed asymmetric Diels-Alder reaction between cyclopentadiene and crotonyl-1,3-oxazolidin-2-one. The Diels-Alder reaction using 15 mol % of 1,1'(2,2'-bisbenzoylamino)binaphthalene . Yb(OTf)(3). 2i-Pr2NEt afforded the adduct with high enantioselectivity (97 % yield, endo/exo = 91/9, > 98 % ee for the endo adduct). (C) 1999 Elsevier Science Ltd. Ail rights reserved.

引用

页码：1555 / 1558

页数：4

共 16 条

[1] Enantioselective ring opening of epoxides with silicon tetrachloride in the presence of a chiral Lewis base [J].

Denmark, SE ;

Barsanti, PA ;

Wong, KT ;

Stavenger, RA .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) :2428-2429

[2] ASYMMETRIC CATALYTIC REDUCTION OF CARBONYL-COMPOUNDS USING C-2 SYMMETRICAL DIAMINES AS CHIRAL LIGANDS [J].

GAMEZ, P ;

FACHE, F ;

LEMAIRE, M .

TETRAHEDRON-ASYMMETRY, 1995, 6 (03) :705-718

[3] CATALYTIC ASYMMETRIC DIELS-ALDER REACTIONS [J].

KAGAN, HB ;

RIANT, O .

CHEMICAL REVIEWS, 1992, 92 (05) :1007-1019

[4] ASYMMETRIC DIELS-ALDER REACTIONS CATALYZED BY CHIRAL LANTHANIDE(III) TRIFLUOROMETHANESULFONATES - UNIQUE STRUCTURE OF THE TRIFLATE AND STEREOSELECTIVE SYNTHESIS OF BOTH ENANTIOMERS USING A SINGLE CHIRAL SOURCE AND A CHOICE OF ACHIRAL LIGANDS [J].

KOBAYASHI, S ;

ISHITANI, H ;

HACHIYA, I ;

ARAKI, M .

TETRAHEDRON, 1994, 50 (40) :11623-11636

[5] ASYMMETRIC DIELS-ALDER REACTION CATALYZED BY A CHIRAL YTTERBIUM TRIFLUOROMETHANESULFONATE [J].

KOBAYASHI, S ;

HACHIYA, I ;

ISHITANI, H ;

ARAKI, M .

TETRAHEDRON LETTERS, 1993, 34 (28) :4535-4538

[6] CHARACTERIZATION OF CHIRAL YTTERBIUM AND SCANDIUM CATALYSTS BASED ON THEIR TRIFLUOROMETHANESULFONATES IN ASYMMETRIC DIELS-ALDER REACTIONS [J].

KOBAYASHI, S ;

ISHITANI, H ;

ARAKI, M ;

HACHIYA, I .

TETRAHEDRON LETTERS, 1994, 35 (34) :6325-6328

[7] LANTHANIDE(III)-CATALYZED ENANTIOSELECTIVE DIELS-ALDER REACTIONS - STEREOSELECTIVE SYNTHESIS OF BOTH ENANTIOMERS BY USING A SINGLE CHIRAL SOURCE AND A CHOICE OF ACHIRAL LIGANDS [J].

KOBAYASHI, S ;

ISHITANI, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (09) :4083-4084

[8]

Kondo K, 1998, SYNLETT, P725

[9]

Nagata T, 1996, CHEM PHARM BULL, V44, P451

[10] DIHYDROPYRIDINONE APPROACH TO MANZAMINES - AN EXPEDIENT CONSTRUCTION OF THE TETRACYCLIC CORE OF MANZAMINE-A [J].

NAKAGAWA, M ;

TORISAWA, Y ;

HOSAKA, T ;

TANABE, K ;

DATE, T ;

OKAMURA, K ;

HINO, T .

TETRAHEDRON LETTERS, 1993, 34 (28) :4543-4546

← 1 2 →