Sc(OTf)3-catalyzed one-pot ene-Prins cyclization: a novel synthesis of octahydro-2H-chromen-4-ols

被引：40
|
作者：
Yadav, J. S. [1 ]
Reddy, B. V. Subba [1 ]
Ganesh, A. V. [1 ]
Kumar, G. G. K. S. Narayana [1 ]
机构：
[1] Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India
来源：
TETRAHEDRON LETTERS | 2010年 / 51卷 / 22期
关键词：
Citronellal; ene-Prins cyclization; Isopulegol; Aldehydes; Octahydro-2H-chromen-4-ols; DIASTEREOSELECTIVE SYNTHESIS; FORMAL SYNTHESIS; EXPEDITIOUS SYNTHESIS; ORGANIC-SYNTHESIS; 3-COMPONENT; TETRAHYDROPYRANS; STEREOCENTERS; CATALYSIS; ALCOHOLS; SEQUENCE;
D O I：
10.1016/j.tetlet.2010.03.100
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
(R)-Citronellal undergoes initial ene reaction followed by Prins cyclization with aldehydes in the presence of 5 mol % of scandium triflate at ambient temperature to furnish octahydro-2H-chromen-4-ols in good yields and with high cis-selectivity. The use of scandium triflate makes this procedure simple, more convenient, and practical. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2963 / 2966
页数：4
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