An efficient synthesis of optically active vicinal diamine arrays via palladium-catalyzed C-O to C-N bond transformation

Synthesis

Volumn , Issue 9, 2004, Pages 1325-1330

  Oshitari, Tetsuta ^a   Akagi, Rumiko ^a   Mandai, Tadakatsu ^a  

^a KURASHIKI UNIVERSITY OF SCIENCE AND THE ARTS   (Japan)

Author keywords

Syn and anti 4 t butoxycarbamoyl 3 hydroxy 1 alkenes; trans imidazolidin 2 ones; allylpalladium complex

Indexed keywords

CATALYSIS; CHEMICAL BONDS; OPTICAL ENGINEERING; PALLADIUM; SYNTHESIS (CHEMICAL);

BOND TRANSFORMATION; VICINAL DIAMINE ARRAYS;

ARRAYS;

DIAMINE DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; ENANTIOSELECTIVITY; OPTICAL ROTATION; PHASE TRANSITION; REACTION ANALYSIS; SYNTHESIS;

EID: 3042709613     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-822377     Document Type: Article

References (12)

1. Lucet, D.; Gall, T. L.; Mioskowski, C. Angew. Chem. Int. Ed. 1998, 37, 2580.
2. Tsuritani, N.; Yamada, K.; Yoshikawa, N.; Shibasaki, M. Chem. Lett. 2002, 276; and references therein.
3. Huang, P.-Q.; Liu, L.-X.; Wei, B.-G.; Ruan, Y.-P. Org. Lett. 2003, 5, 1927; and references therein.
4. Yamazaki, N.; Atobe, M.; Kibayashi, C. Tetrahedron Lett. 2002, 43, 7979; and references therein.
5. For examples: (a) Reetz, M. T.; Jaeger, R.; Drewlies, R.; Hübel, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 103. (b) Gonda, J.; Heiland, A.-C.; Ernst, B.; Bellus, D. Synthesis 1993, 729. Doherty, A. M.; Kornberg, B. E.; Reily, M. D. J. Org. Chem. 1993, 58, 795.
6. For examples: (a) Reetz, M. T.; Jaeger, R.; Drewlies, R.; Hübel, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 103. (b) Gonda, J.; Heiland, A.-C.; Ernst, B.; Bellus, D. Synthesis 1993, 729. Doherty, A. M.; Kornberg, B. E.; Reily, M. D. J. Org. Chem. 1993, 58, 795.
7. For examples: (a) Reetz, M. T.; Jaeger, R.; Drewlies, R.; Hübel, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 103. (b) Gonda, J.; Heiland, A.-C.; Ernst, B.; Bellus, D. Synthesis 1993, 729. Doherty, A. M.; Kornberg, B. E.; Reily, M. D. J. Org. Chem. 1993, 58, 795.
8. Oshitari, T.; Mandai, T. Synlett 2003, 2374.
9. Relevant works based on a similar concept have been reported; that is, palladium-catalyzed reaction of a vinyl epoxide or a 4-pentene-1,3-diol carbonate in the presence of an isocyanate provides an initial zwitterion of π-allylpalladium complex whose oxygen anion is then trapped with isocyanate to give a second π-allylpalladium complex bearing a nitrogen nucleophile tethered to the oxygen. Intramolecular attack of the nitrogen nucleophile to the π-allylpalladium complex furnishes a five- or six-membered carbamate: (a) Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1987, 109, 3792. (b) Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1988, 110, 7933. Bando, T.; Harayama, H.; Fukazawa, Y.; Shiro, M.; Fugami, K.; Tanaka, S.; Tamaru, Y. J. Org. Chem. 1994, 59, 1465.
10. Relevant works based on a similar concept have been reported; that is, palladium-catalyzed reaction of a vinyl epoxide or a 4-pentene-1,3-diol carbonate in the presence of an isocyanate provides an initial zwitterion of π-allylpalladium complex whose oxygen anion is then trapped with isocyanate to give a second π-allylpalladium complex bearing a nitrogen nucleophile tethered to the oxygen. Intramolecular attack of the nitrogen nucleophile to the π-allylpalladium complex furnishes a five- or six-membered carbamate: (a) Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1987, 109, 3792. (b) Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1988, 110, 7933. Bando, T.; Harayama, H.; Fukazawa, Y.; Shiro, M.; Fugami, K.; Tanaka, S.; Tamaru, Y. J. Org. Chem. 1994, 59, 1465.
11. Relevant works based on a similar concept have been reported; that is, palladium-catalyzed reaction of a vinyl epoxide or a 4-pentene-1,3-diol carbonate in the presence of an isocyanate provides an initial zwitterion of π-allylpalladium complex whose oxygen anion is then trapped with isocyanate to give a second π-allylpalladium complex bearing a nitrogen nucleophile tethered to the oxygen. Intramolecular attack of the nitrogen nucleophile to the π-allylpalladium complex furnishes a five- or six-membered carbamate: (a) Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1987, 109, 3792. (b) Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1988, 110, 7933. Bando, T.; Harayama, H.; Fukazawa, Y.; Shiro, M.; Fugami, K.; Tanaka, S.; Tamaru, Y. J. Org. Chem. 1994, 59, 1465.
12. Dunn, P. J.; Häner, R.; Rapoport, H. J. Org. Chem. 1990, 55, 5017.