Allylation of aldehydes and imines:: Promoted by reuseable polymer-supported sulfonamide of N-glycine

被引：57
作者：
Li, GL [1 ]
Zhao, G [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Lab Modern Synth Organ Chem, Shanghai 200032, Peoples R China
来源：
ORGANIC LETTERS | 2006年 / 8卷 / 04期
关键词：
D O I：
10.1021/ol0528235
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A allylation of aldehydes and imines (generated in situ from aldehydes and amines) with allyltributyltin promoted by recoverable and reusable the polymer-supported sulfonamide of N-glycine has been developed. Good to high yields were obtained in various cases. Most of the SnBu3 residue can be recovered as Bu3SnCl. Highly stereoselective synthesis of N-Boc-(2S,3S)-3-hydroxy-2-phenylpiperidine 7 was achieved by using the P4a-mediated allylation of Boc-L-phenylglycinal as a key step.
引用
收藏
页码：633 / 636
页数：4
相关论文
共 50 条
[1]  
ADAV JB, 2002, TETRAHEDRON LETT, V43, P6245
[2]  
Akiyama T, 1998, SYNLETT, P273
[3]  
[Anonymous], EUR J ORG CHEM
[4]   Three component synthesis of homoallylic amines. Efficient catalysis by lanthanum triflate/benzoic acid [J].
Aspinall, HC ;
Bissett, JS ;
Greeves, N ;
Levin, D .
TETRAHEDRON LETTERS, 2002, 43 (02) :323-325
[5]   Stereoselective synthesis of L-733,060 [J].
Bhaskar, G ;
Rao, BV .
TETRAHEDRON LETTERS, 2003, 44 (05) :915-917
[6]   An efficient stereoselective synthesis of (2S,3S)-3-hydroxy-2-phenylpiperidine [J].
Bodas, MS ;
Upadhyay, PK ;
Kumar, P .
TETRAHEDRON LETTERS, 2004, 45 (05) :987-988
[7]   Stereoselective synthesis of (2S,3S)-3-hydroxy-2-phenylpiperidines, precursors of non-peptidic substance P antagonists [J].
Calvez, O ;
Langlois, N .
TETRAHEDRON LETTERS, 1999, 40 (39) :7099-7100
[8]  
Chen JX, 1996, SYNLETT, P877
[9]   Highly efficient allylation of aldehydes and three-component synthesis of homoallylamines using bismuth triflate catalyst [J].
Choudary, BM ;
Chidara, S ;
Sekhar, CVR .
SYNLETT, 2002, (10) :1694-1696
[10]  
Cossy J, 2001, SYNLETT, P629
12345