Stereoselective Diels-Alder reactions of chiral anthracenes

被引：46

作者：

Sanyal, A ^{[1
]}

Snyder, JK ^{[1
]}

机构：

[1] Boston Univ, Dept Chem, Boston, MA 02215 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 16期

关键词：

D O I：

10.1021/ol006206m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Various chiral (9-anthryl)carbinol templates undergo Diels-Alder cycloadditions with a variety of symmetric and nonsymmetric dienophiles with excellent pi-facial selectivity and regioselectivity, under both thermal and Lewis acid catalyzed conditions.

引用

页码：2527 / 2530

页数：4

共 30 条

[1] Enantiopure building blocks for marine natural products via differentiation of enantiotopic groups
Beil, W
Jones, PG
Nerenz, F
Winterfeldt, E
[J]. TETRAHEDRON, 1998, 54 (26) : 7273 - 7292
[2] STEREOSELECTIVE PIG-LIVER ESTERASE-CATALYZED HYDROLYSIS OF RIGID BICYCLIC MESO-DIESTERS - PREPARATION OF OPTICALLY PURE 4,7-EPOXYTETRA-HYDROPHTHALIDES AND HEXA-HYDROPHTHALIDES
BLOCH, R
GUIBEJAMPEL, E
GIRARD, C
[J]. TETRAHEDRON LETTERS, 1985, 26 (34) : 4087 - 4090
[3] SYNTHESIS OF BOTH ENANTIOMERS OF GAMMA-SUBSTITUTED ALPHA, BETA-UNSATURATED GAMMA-LACTONES
BLOCH, R
GILBERT, L
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (20) : 4603 - 4605
[4] Use of 9-anthrylcarbinol derivatives as chiral auxiliaries .2. Asymmetric 1,3-dipolar cycloaddition
Carriere, A
Virgili, A
Figueredo, M
[J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (10) : 2793 - 2796
[5] Complete diastereofacial selective cycloaddition of new sulfinyl dienophiles (Ss)-and (Rs)-(-)menthyl alpha-(2-methoxyphenylsulfoxyl)acylate with anthracene under chelation control
Chau, TY
Lin, HC
Hu, WH
[J]. SYNTHETIC COMMUNICATIONS, 1996, 26 (10) : 1867 - 1874
[6] STRUCTURAL EFFECTS CONTROLLING THE RATE OF THE RETRO-DIELS-ALDER REACTION IN ANTHRACENE CYCLOADDUCTS
CHUNG, YS
DUERR, BF
MCKELVEY, TA
NANJAPPAN, P
CZARNIK, AW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (05) : 1018 - 1032
[7] A NEW SYSTEM FOR CATALYTIC ENANTIOSELECTIVE REDUCTION OF ACHIRAL KETONES TO CHIRAL ALCOHOLS - SYNTHESIS OF CHIRAL ALPHA-HYDROXY ACIDS
COREY, EJ
BAKSHI, RK
[J]. TETRAHEDRON LETTERS, 1990, 31 (05) : 611 - 614
[8] THE FACE SELECTIVITY DIRECTED BY AN ALLYLIC GROUP OF A DIENE IN THE DIELS-ALDER REACTION IS REVERSED FROM THAT OF A DIENOPHILE
FRANCK, RW
ARGADE, S
SUBRAMANIAM, CS
FRECHET, DM
[J]. TETRAHEDRON LETTERS, 1985, 26 (27) : 3187 - 3190
[9] GERSTENBERGER I, 1939, EUR J ORG CHEM, V4, P643
[10] Stereoselective Diels-Alder reactions of hexachlorocyclopentadiene with chiral alkenes: New insights into the ''inside-alkoxy'' model of stereoselectivity
Haller, J
Niwayama, S
Duh, HY
Houk, KN
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) : 5728 - 5731

← 1 2 3 →