Short and Efficient Asymmetric Synthesis of (−)-α-Conhydrine†

作者: Arnaud Voituriez , Franck Ferreira , Fabrice Chemla

DOI: 10.1021/JO070760T

关键词:

摘要: The short and efficient synthesis of (-)-alpha-conhydrine was accomplished with 41% overall yield in seven steps high diastereo- enantioselectivity. anti-stereochemistry the two stereogenic centers has been confirmed by single-crystal X-ray analysis an intermediate.

参考文章(11)
Derek A. Cogan, Guangcheng Liu, Kyungjin Kim, Bradley J. Backes, Jonathan A. Ellman, Catalytic Asymmetric Oxidation of tert-Butyl Disulfide. Synthesis of tert-Butanesulfinamides, tert-Butyl Sulfoxides, and tert-Butanesulfinimines Journal of the American Chemical Society. ,vol. 120, pp. 8011- 8019 ,(1998) , 10.1021/JA9809206
Yukio Masaki, Toshihiro Imaeda, Kinnosuke Nagata, Hirohisa Oda, Akichika Ito, Enantiospecific synthesis of optically active natural (+)-conhydrine from (S,S)-tartaric acid Tetrahedron Letters. ,vol. 30, pp. 6395- 6396 ,(1989) , 10.1016/S0040-4039(01)93904-8
Gabor Fodor, Eberhard Bauerschmidt, A direct, stereoselective synthesis of optically active conhydrines Journal of Heterocyclic Chemistry. ,vol. 5, pp. 205- 209 ,(1968) , 10.1002/JHET.5570050209
Andrew G. Jamieson, Andrew Sutherland, Ether-directed, stereoselective aza-claisen rearrangements: Synthesis of the piperidine alkaloid, α-conhydrine Organic Letters. ,vol. 9, pp. 1609- 1611 ,(2007) , 10.1021/OL070424Z
Jared W. Evans, Jonathan A. Ellman, Stereoselective Synthesis of 1,2-Disubstituted β-Amino Alcohols by Nucleophilic Addition to N-tert-Butanesulfinyl α-Alkoxyaldimines Journal of Organic Chemistry. ,vol. 68, pp. 9948- 9957 ,(2003) , 10.1021/JO035224P
Giovanni. Casiraghi, Franca. Zanardi, Gloria. Rassu, Pietro. Spanu, Stereoselective Approaches to Bioactive Carbohydrates and Alkaloids-With a Focus on Recent Syntheses Drawing from the Chiral Pool Chemical Reviews. ,vol. 95, pp. 1677- 1716 ,(1995) , 10.1021/CR00038A001