4S,5S-[bis(carbethoxy)]-2-ethenyl-1,3,2-dioxaborolane: A novel enantioselective dienophile

被引：23

作者：

Bonk, JD

Avery, MA

机构：

[1] UNIV MISSISSIPPI,SCH PHARM,DEPT MED CHEM,UNIVERSITY,MS 38677

[2] UNIV MISSISSIPPI,DEPT CHEM,UNIVERSITY,MS 38677

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 08期

关键词：

D O I：

10.1016/S0957-4166(97)00122-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The novel chiral vinyl boronate (+)-1 was utilized as a dienophile in a series of [4+2] cycloadditions. The intermediate cyclized products obtained were oxidized directly (H2O2, NaOH). The resulting alcohols displayed enantiomeric excesses of 7-33%. A slight preference for the endo configuration was observed, in agreement with previous results. (C) 1997 Elsevier Science Ltd.

引用

页码：1149 / 1152

页数：4

共 18 条

[1] [Anonymous], ORG REACT
[2] EVANS DA, 1972, TETRAHEDRON LETT, V13, P121
[3] CHIRAL (ACYLOXY)BORANE (CAB) - A POWERFUL AND PRACTICAL CATALYST FOR ASYMMETRIC DIELS-ALDER REACTIONS
FURUTA, K
SHIMIZU, S
MIWA, Y
YAMAMOTO, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) : 1481 - 1483
[4] MARTIN JG, 1961, CHEM REV, P537
[5] VINYLBORONATES BETA-SUBSTITUTED BY AN ELECTRON WITHDRAWING GROUP - SYNTHESIS AND DIELS-ALDER REACTIVITY OF A NEW TYPE OF ELECTRON DEFICIENT OLEFINS
MARTINEZFRESNEDA, P
VAULTIER, M
[J]. TETRAHEDRON LETTERS, 1989, 30 (22) : 2929 - 2932
[6] NORBORNENEBORONATES
MATTESON, DS
WALDBILL.JO
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (02) : 366 - &
[7] RADICAL-CATALYZED ADDITIONS TO ALPHA,BETA-UNSATURATED BORONIC ESTERS
MATTESON, DS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (16) : 4228 - 4233
[8] NARASAKA K, 1992, TETRAHEDRON, V48, P5743
[9] NARASAKA K, 1991, SYNTHESIS-STUTTGART, P1
[10] NOIRET N, 1992, J CHEM SOC CHEM COMM, P1105

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