New Metal-Free One-Pot Synthesis of Substituted Allenes from Enones

被引:27
作者
Tang, Meng
Fan, Chun-An
Zhang, Fu-Min
Tu, Yong-Qiang [1 ]
Zhang, Wen-Xue
Wang, Ai-Xia
机构
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
关键词
D O I
10.1021/ol802445p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new metal-free, one-pot synthesis of substituted allenes from enones was discovered for the first time, in which a tertiary amine as a base was found to be an effective promoter in such novel transformations. The present synthetic protocol proceeded readily with high compatibility of sensitive functional groups, and it provides a new efficient way to access a series of synthetically important allenes without the use of metallic reagents or catalysts.
引用
收藏
页码:5585 / 5588
页数:4
相关论文
共 59 条
[1]   A new protocol for the in situ generation of aromatic, heteroaromatic, and unsaturated diazo compounds and its application in catalytic and asymmetric epoxidation of carbonyl compounds. Extensive studies to map out scope and limitations, and rationalization of diastereo- and enantioselectivities [J].
Aggarwal, VK ;
Alonso, E ;
Bae, I ;
Hynd, G ;
Lydon, KM ;
Palmer, MJ ;
Patel, M ;
Porcelloni, M ;
Richardson, J ;
Stenson, RA ;
Studley, JR ;
Vasse, JL ;
Winn, CL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10926-10940
[2]  
[Anonymous], 2002, HDB ORGANOPALLADIUM
[3]   α′-Hydroxy-α,β-unsaturated tosylhydrazones:: Preparation and use as intermediates for carbonyl and enone transpositions [J].
Baptistella, LHB ;
Alexio, AM .
SYNTHETIC COMMUNICATIONS, 2002, 32 (19) :2937-2950
[4]   Nucleophilic transition metal based cyclization of allenes [J].
Bates, RW ;
Satcharoen, V .
CHEMICAL SOCIETY REVIEWS, 2002, 31 (01) :12-21
[5]   Allenic compounds and isothiocyanates as key building units in the synthesis of heterocycles [J].
Brandsma, L ;
Nedolya, NA .
SYNTHESIS-STUTTGART, 2004, (05) :735-745
[6]   Synthesizing allenes today (1982-2006) [J].
Brummond, Kay M. ;
DeForrest, Jolie E. .
SYNTHESIS-STUTTGART, 2007, (06) :795-818
[7]   Strategy for the preparation of allenes from alpha,beta-unsaturated and saturated ketones via enol phosphates [J].
Brummond, KM ;
Dingess, EA ;
Kent, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (18) :6096-6097
[8]  
BRUNEAU C, 1995, COMPREHENSIVE ORGANI, V1
[9]  
BRUNEAU C, 2005, COMPREHENSIVE ORGANI, V1
[10]  
BURTON BS, 1887, DTSCH CHEM GES, V20, P145