LEWIS ACID-PROMOTED REACTIONS OF UNSYMMETRICALLY SUBSTITUTED STILBENES WITH 2-METHOXY-1,4-BENZOQUINONES - STEREOSELECTIVE SYNTHESIS OF TRANS-2,3-DIARYL-2,3-DIHYDROBENZOFURANS

被引：39

作者：

ENGLER, TA

GFESSER, GA

DRANEY, BW

机构：

[1] Department of Chemistry, University of Kansas, Lawrence

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 12期

关键词：

D O I：

10.1021/jo00117a021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lewis acid (SnCl4 or Ti(IV))-promoted reactions of 2-methoxy-1,4-benzoquinones with substituted (E)-4-methoxystilbenes stereoselectively yield trans-2-(4'-methoxyphenyl)-3-aryl-2,3-dihydrobenzofuran-5-ols in good yield.

引用

页码：3700 / 3706

页数：7

共 10 条

[1] Lewis Acid Mediated [3+2] Coupling of Masked Benzoquinones with Styrenes: Facile Synthesis of 2,3-Dihydrobenzofurans
Sharma, Shivangi
Parumala, Santosh Kumar Reddy
Peddinti, Rama Krishna
SYNLETT, 2017, 28 (02) : 239 - 244
[2] A facile domino protocol for the stereoselective synthesis of trans-2,3-dihydrobenzofurans and cis-5,6-dihydrofuro[2,3-d]pyrimidines
Vinosha, Beermohamed
Perumal, Subbu
Renuga, Subbiah
Almansour, Abdulrahman I.
TETRAHEDRON LETTERS, 2012, 53 (08) : 962 - 966
[3] SWITCHABLE REGIOSELECTIVITY IN LEWIS ACID-PROMOTED REACTIONS OF 1,4-BENZOQUINONE MONOIMIDES WITH STYRENYL SYSTEMS - SELECTIVE SYNTHESES OF EITHER 2-ARYL-2,3-DIHYDROBENZOFURANS OR 2-ARYL-2,3-DIHYDROINDOLES
ENGLER, TA
CHAI, WY
LYNCH, KO
TETRAHEDRON LETTERS, 1995, 36 (39) : 7003 - 7006
[4] Radical-induced expeditious stereoselective synthesis of 2-alkyl 3-allyl trans-2,3-dihydrobenzofurans (TADHBs)
Sarkar, Debayan
Sahoo, Sushree Ranjan
SYNTHETIC COMMUNICATIONS, 2018, 48 (05) : 574 - 581
[5] Regiocontrolled Lewis acid-promoted reactions of 1,4-benzoquinone mono- and bisimides with styrenyl systems, selective syntheses of either 2-aryl-2,3-dihydrobenzofurans or 2-aryl-2,3-dihydroindoles.
Engler, TA
Chai, WY
Meduna, SP
Lynch, KO
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 211 : 311 - ORGN
[6] K3PO4-promoted domino reactions: diastereoselective synthesis of trans-2,3-dihydrobenzofurans from salicyl N-tert-butanesulfinyl imines and sulfur ylides
Zhang, Minxuan
Lu, Tianyu
Zhao, Yun
Xie, Guixian
Miao, Zhiwei
RSC ADVANCES, 2019, 9 (21): : 11978 - 11985
[7] STEREOSPECIFIC LEWIS ACID-PROMOTED REACTIONS OF STYRENYL SYSTEMS WITH 2-ALKOXY-(6-ALKYL)-1,4-BENZOQUINONES - SCOPE, LIMITATIONS, AND SYNTHETIC APPLICATIONS
ENGLER, TA
COMBRINK, KD
LETAVIC, MA
LYNCH, KO
RAY, JE
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (22): : 6567 - 6587
[8] Lewis acid-controlled regioselectivity in reactions of styrenyl systems with benzoquinone monoimides: New regioselective syntheses of substituted 2-aryl-2,3-dihydrobenzofurans, 2-aryl-2,3-dihydroindoles, and 2-arylindoles
Engler, TA
Chai, WY
LaTessa, KO
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26): : 9297 - 9308
[9] Lewis acid-promoted reactions of styrenyl systems with benzoquinone bisimines: New regioselective syntheses of substituted 2-aryl-2,3-dihydroindoles and 2-arylindoles
Engler, TA
Meduna, SP
LaTessa, KO
Chai, WY
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24): : 8598 - 8603
[10] Asymmetric reactions of 2-methoxy-1,4-benzoquinones with styrenyl systems: Enantioselective syntheses of 8-aryl-3-methoxybicyclo [4.2.0]oct-3-en-2,5-diones, 7-aryl-3-hydroxybicyclo[3.2.1]oct-3-en-2,8-diones, 2-aryl-6-methoxy-2,3-dihydrobenzofuran-5-ols, and pterocarpans
Engler, TA
Letavic, MA
Iyengar, R
LaTessa, KO
Reddy, JP
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07): : 2391 - 2405

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