Rhodium-catalyzed asymmetric ring opening of oxabicyclic alkenes with phenols

被引：100

作者：

Lautens, M ^{[1
]}

Fagnou, K ^{[1
]}

Taylor, M ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Lash Miller Labs, Toronto, ON M5H 3H6, Canada

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 12期

关键词：

D O I：

10.1021/ol005729r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The scope of the rhodium-catalyzed asymmetric ring opening reaction of oxabenzonorbornadiene has been extended to include phenolic nucleophiles. The enanatioenriched, functionalized dihydronaphthalene products are highly valuable intermediates for which no other practical methods of preparation are available. A new catalyst system has been developed which allows the use of less reactive o-halophenols. The utility of these products has been demonstrated through their application in the synthesis of benzofuran polycyclic materials.

引用

页码：1677 / 1679

页数：3

共 20 条

[1] Synthesis and applications of a new class of C2 symmetric phosphorus donor ligand for asymmetric catalysis.
Brenchley, G
Fedouloff, M
Merifield, E
Wills, M
[J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (10) : 2809 - 2812
[2] GOUX C, 1992, SYNLETT, P725
[3] Iida T, 1998, ANGEW CHEM INT EDIT, V37, P2223, DOI 10.1002/(SICI)1521-3773(19980904)37:16<2223::AID-ANIE2223>3.0.CO
[4] 2-Z
[5] Johnson B. M., 1996, ANAL PROFILES DRUG S, V24, P443, DOI 10.1016/S0099-5428(08)60700-5
[6] An efficient method for 4 beta-anilino-4'-demethylepipodophyllotoxins: Synthesis of NPF and W-68
Kamal, A
Gayatri, NL
[J]. TETRAHEDRON LETTERS, 1996, 37 (19) : 3359 - 3362
[7] SYNTHETIC STUDIES OF THE ANGUCYCLINE ANTIBIOTICS - STEREOCONTROLLED ASSEMBLY OF THE SF 2315B RING-SYSTEM
KIM, K
GUO, Y
SULIKOWSKI, GA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) : 6866 - 6871
[8] HOMOGENEOUS ASYMMETRIC HYDROGENATION OF FUNCTIONALIZED KETONES
KITAMURA, M
OHKUMA, T
INOUE, S
SAYO, N
KUMOBAYASHI, H
AKUTAGAWA, S
OHTA, T
TAKAYA, H
NOYORI, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (02) : 629 - 631
[9] General strategy toward the tetrahydronaphthalene skeleton. An expedient total synthesis of sertraline
Lautens, M
Rovis, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (16) : 5246 - 5247
[10] Scope of the nickel catalyzed asymmetric reductive ring opening reaction. Synthesis of enantiomerically enriched cyclohexenols.
Lautens, M
Rovis, T
[J]. TETRAHEDRON, 1998, 54 (07) : 1107 - 1116

← 1 2 →