Organosilanes in Copper-Mediated Conjugate Reductions and Reductive Aldol Reactions

Abstract

Organosilanes have been used to synthesize and regenerate copper hydrides, and have been employed as stoichiometric reductants in the copper-catalyzed reductions of a variety of activated olefins. Reductive aldol condensations and cyclizations using organosilanes and transition metal catalysts, including copper hydrides, have also been achieved.

organosilanes - copper conjugate reductions - aldol reactions

References

<A NAME="RC04504SS-1A">1a</A> Ojima I. Catalytic Asymmetric Synthesis   VCH; New York: 1993.  Chap 6.

<A NAME="RC04504SS-1B">1b</A> Larock RC. Comprehensive Organic Transformations   2nd ed:  Wiley-VCH; New York: 1999.  p.13-26  

<A NAME="RC04504SS-2">2</A> For a review on the complementary hydrosilylation of carbonyl compounds by organosilanes, see: Carpentier JF. Bette V. Curr. Org. Chem.  2002,  6:  913 

<A NAME="RC04504SS-3">3</A> Mahoney WS. Brestensky DM. Stryker JM. J. Am. Chem. Soc.  1988,  110:  291 

<A NAME="RC04504SS-4">4</A> Mori A. Fujita A. Nishihara Y. Hiyama T. Chem. Commun.  1997,  2159 

<A NAME="RC04504SS-5">5</A> Ito H. Ishizuka T. Arimoto K. Miura K. Hosomi A. Tetrahedron Lett.  1997,  38:  8887 

<A NAME="RC04504SS-6A">6a</A> Lipshutz BH. Keith J. Papa P. Vivian R. Tetrahedron Lett.  1998,  39:  4627 

<A NAME="RC04504SS-6B">6b</A> Lipshutz BH. Chrisman W. Noson K. Papa P. Sclafani JA. Vivian RW. Keith JM. Tetrahedron  2000,  56:  2779 

<A NAME="RC04504SS-7A">7a</A> Appella DH. Moritani Y. Shintani R. Ferreira EM. Buchwald SL. J. Am. Chem. Soc.  1999,  121:  9473 

<A NAME="RC04504SS-7B">7b</A> Moritani Y. Appella DH. Jurkauskas V. Buchwald SL. J. Am. Chem. Soc.  2000,  122:  6797 

<A NAME="RC04504SS-7C">7c</A> Lipshutz BH. Servesko JM. Angew. Chem. Int. Ed.  2003,  42:  4789 

<A NAME="RC04504SS-7D">7d</A> Hughes G. Kimura M. Buchwald SL. J. Am. Chem. Soc.  2003,  125:  11253 

<A NAME="RC04504SS-7E">7e</A> Czekelius C. Carreira EM. Angew. Chem. Int. Ed.  2003,  42:  4793 

<A NAME="RC04504SS-8A">8a</A> Mahoney WS. Stryker JM. J. Am. Chem. Soc.  1989,  111:  8818 

<A NAME="RC04504SS-8B">8b</A> Goeden GV. Caulton KG. J. Am. Chem. Soc.  1981,  103:  7354 

<A NAME="RC04504SS-8C">8c</A> Brestensky DM. Huseland DE. McGettigan C. Stryker JM. Tetrahedron Lett.  1988,  29:  3749 

<A NAME="RC04504SS-9">9</A> Chiu P. Li Z. Fung KCM. Tetrahedron Lett.  2003,  44:  455 

<A NAME="RC04504SS-10">10</A> p-Tol-BINAP: 2,2′-bis(di-p-tolylphosphino)-1,1′-binaphthyl; BIPHEMP: 2,2′-bis(diphenylphosphino)-6,6′-dimethyl-1,1′-biphenyl; JOSIPHOS: 1-[2-diphenyl]-phosphanyl]ferrocenyl]ethyldicyclohexyl-phosphane; BINAP: 2,2′-bis(dipenylphosphino)-1,1′-binaphthyl; DuPhos: 1,2-bis(2,5)-dimethylphosphalano)benzene, pybox: 2,6-bis(oxazolinyl)pyridine

<A NAME="RC04504SS-11">11</A> Yun J. Buchwald SL. Org. Lett.  2001,  3:  1129 

<A NAME="RC04504SS-12">12</A> Revis A. Hilty TK. Tetrahedron Lett.  1987,  28:  4809 

<A NAME="RC04504SS-13">13</A> Matsuda I. Takahasi K. Sato S. Tetrahedron Lett.  1990,  31:  5331 

<A NAME="RC04504SS-14">14</A> Taylor SJ. Morken JP. J. Am. Chem. Soc.  1999,  121:  12202 

<A NAME="RC04504SS-15">15</A> Kiyooka S. Shimizu A. Torii S. Tetrahedron Lett.  1998,  39:  5237 

<A NAME="RC04504SS-16A">16a</A> Taylor SJ. Duffey MO. Morken JP. J. Am. Chem. Soc.  2000,  122:  4528 

<A NAME="RC04504SS-16B">16b</A> Zhao CX. Bass J. Morken JP. Org. Lett.  2001,  3:  2839 

<A NAME="RC04504SS-16C">16c</A> Zhao CX. Duffey MO. Taylor SJ. Morken JP. Org. Lett.  2001,  3:  1829 

<A NAME="RC04504SS-17">17</A> Isayama S. Mukaiyama T. Chem. Lett.  1989,  2005 

<A NAME="RC04504SS-18A">18a</A> Baik TG. Luis AL. Wang LC. Krische MJ. J. Am. Chem. Soc.  2001,  123:  5112 

<A NAME="RC04504SS-18B">18b</A> Wang LC. Jang HY. Baik TG. Luis AL. Lynch V. Krische MJ. J. Am. Chem. Soc.  2002,  124:  9448 

<A NAME="RC04504SS-18C">18c</A> Huddleston RR. Krische MJ. Synlett  2003,  12 

<A NAME="RC04504SS-19A">19a</A> Chiu P. Chen B. Cheng KF. Tetrahedron Lett.  1998,  39:  9299 

<A NAME="RC04504SS-19B">19b</A> Chiu P. Szeto CP. Geng Z. Cheng KF. Tetrahedron Lett.  2001,  42:  4091 

<A NAME="RC04504SS-19C">19c</A> Chiu P. Szeto CP. Geng Z. Cheng KF. Org. Lett.  2001,  3:  1901 

<A NAME="RC04504SS-20C">20c</A> Chiu P. Leung SK. Chem. Commun.  2004,  in press