A highly diastereoselective “super silyl” governed aldol reaction: synthesis of α,β-dioxyaldehydes and 1,2,3-triols

作者: Wafa Gati , Hisashi Yamamoto

DOI: 10.1039/C5SC03307A

关键词:

摘要: A highly diastereoselective approach for the synthesis of protected α,β-dioxyaldehydes derived from (Z)-tris(trimethylsilyl)silyl “super silyl” enol ethers is described. general and syn-stereoselective aldol reaction directed by group catalyzed triflimide (HNTf2) developed providing 1,2,3-triol fragments which can be a useful platform elaboration natural unnatural sugar derivatives.

参考文章(35)
D. A. Evans, J. V. Nelson, T. R. Taber, Stereoselective Aldol Condensations Topics in Stereochemistry, Volume 13. pp. 1- 115 ,(2007) , 10.1002/9780470147221.CH1
Martin T. Mwangi, Michael D. Schulz, Ned B. Bowden, Sequential reactions with Grubbs catalyst and AD-mix-alpha/beta using PDMS thimbles. Organic Letters. ,vol. 11, pp. 33- 36 ,(2009) , 10.1021/OL8022215
Karl B. Lindsay, Stephen G. Pyne, Asymmetric synthesis of (-)-swainsonine, (+)-1,2-di-epi-swainsonine, and (+)-1,2,8-tri-epi-swainsonine. Journal of Organic Chemistry. ,vol. 67, pp. 7774- 7780 ,(2002) , 10.1021/JO025977W
Narayan S Karanjule, Shankar D Markad, Dilip D Dhavale, None, Synthesis of pentahydroxy indolizidine alkaloids using ring closing metathesis: attempts to find the correct structure of uniflorine A. Journal of Organic Chemistry. ,vol. 71, pp. 6273- 6276 ,(2006) , 10.1021/JO060823S
Rainer Mahrwald, Diastereoselection in lewis-Acid-mediated aldol additions. Chemical Reviews. ,vol. 99, pp. 1095- 1120 ,(1999) , 10.1021/CR980415R
Jun-ichi Matsuo, Masahiro Murakami, The Mukaiyama aldol reaction: 40 years of continuous development. Angewandte Chemie. ,vol. 52, pp. 9109- 9118 ,(2013) , 10.1002/ANIE.201303192
Barry M. Trost, Cheyenne S. Brindle, The Direct Catalytic Asymmetric Aldol Reaction Chemical Society Reviews. ,vol. 39, pp. 1600- 1632 ,(2010) , 10.1039/B923537J
Manuel Peifer, Raphaëlle Berger, Valerie W. Shurtleff, Jay C. Conrad, David W. C. MacMillan, A General and Enantioselective Approach to Pentoses: A Rapid Synthesis of PSI-6130, the Nucleoside Core of Sofosbuvir Journal of the American Chemical Society. ,vol. 136, pp. 5900- 5903 ,(2014) , 10.1021/JA502205Q
Teruaki Mukaiyama, Koichi Narasaka, Kazuo Banno, NEW ALDOL TYPE REACTION Chemistry Letters. ,vol. 2, pp. 1011- 1014 ,(1973) , 10.1246/CL.1973.1011
Timothy D. Machajewski, Chi-Huey Wong, The Catalytic Asymmetric Aldol Reaction Angewandte Chemie International Edition. ,vol. 39, pp. 1352- 1375 ,(2000) , 10.1002/(SICI)1521-3773(20000417)39:8<1352::AID-ANIE1352>3.0.CO;2-J