Unprecedented stereoselective synthesis of cyclopenta[b]benzofuran derivatives and their characterisation assisted by aligned media NMR and 13C chemical shift ab initio predictions

被引:26
作者
Riveira, Martin J. [2 ]
Gayathri, Chakicherla [1 ]
Navarro-Vazquez, Armando [3 ]
Tsarevsky, Nicolay V. [4 ]
Gil, Roberto R. [1 ]
Mischne, Mirta P. [2 ]
机构
[1] Carnegie Mellon Univ, Dept Chem, Pittsburgh, PA 15213 USA
[2] Univ Nacl Rosario, Fac Ciencias Bioquim & Farmaceut, Inst Quim Rosario CONICET, RA-2000 Rosario, Santa Fe, Argentina
[3] Univ Vigo, Dept Quim Organ, Vigo 36310, Spain
[4] So Methodist Univ, Dept Chem, Dallas, TX 75275 USA
关键词
RESIDUAL DIPOLAR COUPLINGS; SHIELDING CONSTANTS; ORGANIC-COMPOUNDS; RDCS; CONFIGURATION; ROCAGLAMIDE; ASSIGNMENT; MOLECULES; CHEMISTRY; ALIGNMENT;
D O I
10.1039/c1ob05109a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new approach to the synthesis of cyclopenta[b]benzofuran derivatives via reaction of 1,3-dicarbonyl compounds with alpha, beta, gamma, delta-unsaturated aldehydes is described. The constitution and configuration of the new products have been firmly established by means of residual dipolar couplings (RDCs) and ab initio C-13 NMR chemical shift predictions.
引用
收藏
页码:3170 / 3175
页数:6
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