THE TANDEM CYCLOADDITION CHEMISTRY OF NITROALKENES

被引：12
作者：
DENMARK, SE
SCHNUTE, ME
THORARENSEN, A
MIDDLETON, DS
STOLLE, A
机构：
[1] Department of Chemistry, University of Illinois at Urbana-Champaign Urbana, Illinois
来源：
PURE AND APPLIED CHEMISTRY | 1994年 / 66卷 / 10-11期
基金：
美国国家卫生研究院;
关键词：
D O I：
10.1351/pac199466102041
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Nitroalkenes have proven to be extremely versatile 4pi-components in heterodiene [4+2]-cycloadditions. Our efforts in this area have been intensively methodological with focus on the reaction scope, mechanism, stereoselectivity and transformations of the cycloadducts. The three modes of tandem inter [4+2]/ intra [3+2] cycloaddition, fused, spiro and bridged have been documented. An efficient and highly selective synthesis of (-)-hastanecine has been completed.
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收藏
页码：2041 / 2044
页数：4
相关论文
共 8 条
[1]   INVENTION OF NEW REACTIONS USEFUL IN THE CHEMISTRY OF NATURAL-PRODUCTS [J].
BARTON, DHR ;
ZARD, SZ .
PURE AND APPLIED CHEMISTRY, 1986, 58 (05) :675-684
[2]   TANDEM [4+2]/[3+2]-CYCLOADDITIONS .2. ASYMMETRIC INDUCTION WITH A CHIRAL VINYL ETHER [J].
DENMARK, SE ;
SENANAYAKE, CBW ;
HO, GD .
TETRAHEDRON, 1990, 46 (13-14) :4857-4876
[3]   TANDEM INTER [4 + 2] INTRA [3 + 2] NITROALKENE CYCLOADDITIONS .5. ORIGIN OF THE LEWIS ACID DEPENDENT REVERSAL OF STEREOSELECTIVITY [J].
DENMARK, SE ;
SCHNUTE, ME ;
SENANAYAKE, CBW .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (07) :1859-1874
[4]  
DENMARK SE, 1992, 5TH P INT KYOT C ORG, P215
[5]   2-BENZOYLOXYNITROETHYLENE AS A CIS-2-AMINOETHENOL EQUIVALENT [J].
KRAUS, GA ;
THURSTON, J ;
THOMAS, PJ ;
JACOBSON, RA ;
SU, YZ .
TETRAHEDRON LETTERS, 1988, 29 (16) :1879-1882
[6]   METHYLALUMINUM BIS(2,6-DI-TERT-BUTYL-4-ALKYLPHENOXIDE) - A NEW REAGENT FOR OBTAINING UNUSUAL EQUATORIAL AND ANTI-CRAM SELECTIVITY IN CARBONYL ALKYLATION [J].
MARUOKA, K ;
ITOH, T ;
YAMAMOTO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (15) :4573-4576
[7]  
MULZER J, 1993, SYNTHESIS-STUTTGART, P615
[8]   ORGANOALUMINUM-PROMOTED CLAISEN REARRANGEMENT OF ALLYL VINYL ETHERS [J].
NONOSHITA, K ;
BANNO, H ;
MARUOKA, K ;
YAMAMOTO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (01) :316-322
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