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

页码：2963 / 2966

页数：4

共 50 条

[31] AN ECO-FRIENDLY ONE-POT SYNTHESIS OF 4,4′-(ARYLMETHYLENE)BIS(1H-PYRAZOL-5-OLS) USING [Et3NH][HSO4] AS A RECYCLABLE CATALYST
Zhou, Zhongqiang
Zhang, Yuliang
JOURNAL OF THE CHILEAN CHEMICAL SOCIETY, 2015, 60 (03): : 2992 - 2996
[32] Facile synthesis of HFIP esters-containing 2H-benzopyrans H-benzopyrans through palladium-catalyzed one-pot cyclization/carbonylation using formic acid as the CO source
Wen, Dan
Yao, Boyu
Qi, Xinxin
Wu, Xiao-Feng
JOURNAL OF CATALYSIS, 2024, 436
[33] H3PO4 catalyzed one-pot synthesis of 1,3-diphenyl-1H-pyrazole-4-carbaldehyde to novel 1,3-diphenyl-1H-pyrazole-4-carbonitrile
Choudhare, Tukaram S.
Wagare, Devendra S.
Shirsath, Sagar E.
Netankar, Prashant D.
JOURNAL OF CHEMICAL SCIENCES, 2021, 133 (03)
[34] An ionic liquid catalyzed reusable protocol for one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one under mild conditions
Nagarajan, S.
Shaikh, Tanveer Mahamadali
Kandasamy, Elango
NEW JOURNAL OF CHEMISTRY, 2015, 39 (12) : 9693 - 9699
[35] Experimental and Theoretical Investigation of One-pot Synthesis of 2-Amino-4H-chromenes Catalyzed by Basic-functionalized Ionic Liquids
Wang Yuanyuan
Wu Yuetong
Wang Yu
Dai Liyi
CHINESE JOURNAL OF CHEMISTRY, 2012, 30 (08) : 1709 - 1714
[36] ONE-POT THREE-COMPONENT SYNTHESIS OF 3-METHYL-4-ARYLMETHYLENE-ISOXAZOL-5(4H)-ONES CATALYZED BY SODIUM SULFIDE
Liu, Qing
Hou, Xianming
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2012, 187 (04) : 448 - 453
[37] Three-component, one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones catalyzed by bromodimethylsulfonium bromide
A. Shaabani
A. Maleki
Chemical Papers, 2007, 61 : 333 - 336
[38] Copper Nitrate Catalyzed Three-Component One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-Ones
Wang, Min
Jiang, Heng
Song, Zhiguo
Gong, Hong
PREPARATIVE BIOCHEMISTRY & BIOTECHNOLOGY, 2009, 39 (04) : 372 - 379
[39] Three-component, one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones catalyzed by bromodimethylsulfonium bromide
Shaabani, A.
Maleki, A.
CHEMICAL PAPERS, 2007, 61 (04) : 333 - 336
[40] A novel method for the one-pot three-component synthesis of 2,3-dihydroquinazolin-4(1H)-ones
Salehi, P
Dabiri, M
Zolfigol, MA
Baghbanzadeh, M
SYNLETT, 2005, (07) : 1155 - 1157

← 1 2 3 4 5 →