Carbohydrate-Templated Asymmetric Diels-Alder Reactions of Masked ortho-Benzoquinones for the Synthesis of Chiral Bicyclo[2.2.2]oct-5-en-2-ones

被引：40

作者：

Luo, Shun-Yuan ^{[1
]}

Jang, Yeong-Jiunn ^{[1
]}

Liu, Jing-Yuan ^{[1
]}

Chu, Chrong-Shyua ^{[1
]}

Liao, Chun-Chen ^{[1
]}

Hung, Shang-Cheng ^{[1
]}

机构：

[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 300, Taiwan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 42期

关键词：

asymmetric synthesis; benzoquinones; bicyclic compounds; chiral auxiliaries; cycloaddition;

D O I：

10.1002/anie.200802693

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) A sweet addition: Asymmetric [4 + 2] cycloaddition of masked ortho-benzoquinones with various alkenols by using sugars as chiral auxiliaries (see scheme; Bn: benzyl) affords the optically pure bicyclo[2.2.2]oct-5-en-2-ones with excellent diastereoselectivity and in good yields. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：8082 / 8085

页数：4

共 50 条

[21] Synthesis of 1-hydroxybicyclo[3.2.1]oct-3-en-2-ones by acyloin rearrangement of 1-methoxy- or 1-tert-butyldimethylsilyloxybicyclo[2.2.2]oct-5-en-2-ones
Katayama, S
Hiramatsu, H
Aoe, K
Yamauchi, M
CHEMICAL & PHARMACEUTICAL BULLETIN, 1997, 45 (09) : 1419 - 1427
[22] Tandem oxidative acetalization-intramolecular Diels-Alder reactions of 2-methoxyphenols. Simple synthesis of bicyclo[2.2.2]octenone derivatives
Chu, CS
Lee, TH
Rao, PD
Song, LD
Liao, CC
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (11): : 4111 - 4118
[23] 5,6,7,8-TETRAMETHYLENEBICYCLO[2.2.2]OCT-2-ENE AS BIS(DIENE) IN REPETITIVE DIELS-ALDER REACTIONS
WEGENER, S
MULLEN, K
CHEMISCHE BERICHTE, 1991, 124 (09) : 2101 - 2103
[24] ASYMMETRIC-SYNTHESIS OF CHIRAL CYCLIC AMINO-ACIDS BY DIELS-ALDER REACTIONS OF (2S)-4-METHYLENEOXAZOLIDIN-5-ONES AND (2R)-4-METHYLENEOXAZOLIDIN-5-ONES
PYNE, SG
DIKIC, B
GORDON, PA
SKELTON, BW
WHITE, AH
AUSTRALIAN JOURNAL OF CHEMISTRY, 1993, 46 (01) : 73 - 93
[25] 4-HYDROXYCYCLOPENT-2-EN-1-ONE AND DERIVATIVES AS CHIRAL SYNTHETIC EQUIVALENTS OF CYCLOPENTADIENONE IN ASYMMETRIC DIELS-ALDER REACTIONS
DOLS, PPMA
KLUNDER, AJH
ZWANENBURG, B
TETRAHEDRON, 1994, 50 (28) : 8515 - 8538
[26] CHIRAL LEWIS ACID-CATALYZED ASYMMETRIC DIELS-ALDER REACTIONS OF (E)-1-PHENYLSULFONYL-3-ALKEN-2-ONES WITH CYCLOPENTADIENE
WADA, E
PEI, W
KANEMASA, S
CHEMISTRY LETTERS, 1994, (12) : 2345 - 2348
[27] BILE-ACIDS IN ASYMMETRIC-SYNTHESIS .2. CHOLIC-ACID DERIVED NOVEL CHIRAL AUXILIARIES FOR ASYMMETRIC DIELS-ALDER REACTIONS
MAITRA, U
PACKIARAJAN, M
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (19) : 1469 - 1471
[28] ASYMMETRIC DIELS-ALDER REACTIONS WITH A CHIRAL MALEIC-ANHYDRIDE ANALOG, 5-(1-MENTHYLOXY)-2(5H)-FURANONE
FERINGA, BL
DEJONG, JC
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (05): : 1125 - 1127
[29] Competitive intramolecular Diels-Alder reactions of bis-α,β-unsaturated ester derivatives of enzymatically derived and enantiopure cis-1,2-dihydrocatechols.: Enantiodivergent synthesis of monochiral bicyclo[2.2.2]oct-2-enes
Banwell, MG
Chun, C
Edwards, AJ
Vögtle, MM
AUSTRALIAN JOURNAL OF CHEMISTRY, 2003, 56 (09) : 861 - 869
[30] Dual Behavior of masked o-benzoquinones in intramolecular Diels-Alder reactions.: Expedient synthesis of highly functionalized cis-decalins from 2-methoxyphenols
Hsu, PY
Peddinti, RK
Chittimalla, SK
Liao, CC
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (23): : 9156 - 9167

← 1 2 3 4 5 →