New synthetic technology for the mild and selective one-carbon homologation of hindered aldehydes in the presence of ketones

Organic Letters

Volumn 2, Issue 13, 2000, Pages 1895-1898

  Nicolaou, K C ^a,b   Vassilikogiannakis, Georgios ^a,b   Kranich, Remo ^a,b   Baran, Phil S ^a,b   Zhong, Yong Li ^a,b   Natarajan, Swaminathan ^a,b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000991541     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000102u     Document Type: Article

References (14)

1. Part 1: Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Choi, H.-S.; Yoon, W. H.; He, Y.; Fong, K. C. Angew. Chem., Int. Ed. 1999, 38, 1669. Part 2: Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Fong, K. C.; He, Y.; Yoon, W. H.; Choi, H.-S. Angew. Chem., Int. Ed. 1999, 38, 1676. For the asymmetric total synthesis of the CP molecules, see: Nicolaou, K. C.; Jung, J.-Q.; Yoon, W. H.; He, Y.; Zhong, Y.-L.; Baran, P. S. Angew. Chem., Int. Ed. 2000, 39, 1829.
2. Part 1: Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Choi, H.-S.; Yoon, W. H.; He, Y.; Fong, K. C. Angew. Chem., Int. Ed. 1999, 38, 1669. Part 2: Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Fong, K. C.; He, Y.; Yoon, W. H.; Choi, H.-S. Angew. Chem., Int. Ed. 1999, 38, 1676. For the asymmetric total synthesis of the CP molecules, see: Nicolaou, K. C.; Jung, J.-Q.; Yoon, W. H.; He, Y.; Zhong, Y.-L.; Baran, P. S. Angew. Chem., Int. Ed. 2000, 39, 1829.
3. Part 1: Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Choi, H.-S.; Yoon, W. H.; He, Y.; Fong, K. C. Angew. Chem., Int. Ed. 1999, 38, 1669. Part 2: Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Fong, K. C.; He, Y.; Yoon, W. H.; Choi, H.-S. Angew. Chem., Int. Ed. 1999, 38, 1676. For the asymmetric total synthesis of the CP molecules, see: Nicolaou, K. C.; Jung, J.-Q.; Yoon, W. H.; He, Y.; Zhong, Y.-L.; Baran, P. S. Angew. Chem., Int. Ed. 2000, 39, 1829.
4. Nicolaou, K. C.; Härter, M. W.; Gunzner, J. L.; Nadin A. Liebigs Ann. 1997, 1283.
5. Matteson, D. S. Chem. Rev. 1989, 89, 1535.
6. Bestmann, H. J.; Zimmerman, R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; 1991; Vol. 6, pp 171-198.
7. Nagata, W.; Yoshioka, M.; Okumura, T. Tetrahedron Lett. 1966, 847.
8. Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin. Trans. 1 1975, 1574.
9. Critch, D.; Quintero, L. Chem. Rev. 1989, 89, 1413.
10. 2AlCN was used to avoid Michael addition.
11. 3SnH + AIBN + hv; (e) experiment d followed by silica gel chromatography; (f) 8 + 4-DMAP or imidazole. Experiments a-e led to no reaction and full recovery of 8. Experiment f led to ca. 20% conversion to cyclohexanone after 12 h.
12. Prepared as reported in Japanese Patent application JP 79-38934 (Sumitomo Chemical Co., Ltd., Japan), see also: Chem. Abstr. 94, 139812.
13. Nicolaou, K. C.; Vourloumis, D.; Winssinger, N.; Baran, P. S. Angew. Chem., Int. Ed. 2000, 39, 44.
14. 3SnH (5.0 equiv), and AIBN (0.2 equiv) were added, and the reaction vessel was placed in a 20°C water bath while exposed to light from a nearby sunlamp (simple floodlamp) for 5-20 min (TLC monitoring). The reaction mixture was diluted (10:1 hexanes:EtOAc) and passed through a silica plug to remove tin impurities, and the product was eluted with hexanes:EtOAc (1:1). Flash column chromatography was employed to obtain spectroscopically pure material.