Template-Induced Enantioselectivity in the Reductive Radical Cyclization of 3-(3-Iodopropoxy)propenoic Acid Derivatives Depending on the Binding Motif

Abstract

Different binding motifs HXC=O have been screened in the enantioselective radical cyclization of various linear derivatives of 3-(3-iodopropoxy)propenoic acid. The reactions were performed in the presence of an enantiomerically pure, chiral 1,5,7-trimethyl-3-azabicyclo[3.3.1]nonan-2-one derivative, which acts as a hydrogen-binding template. The cyclized products were obtained in good to excellent yields (66-88%). Enantioselectivities up to 59% ee were achieved.

cyclizations - enantioselectivity - lactams - radical reactions - supramolecular chemistry

References

For reviews, see:

<A NAME="RZ04608SS-1A">1a</A> Zimmerman J. Sibi MP. Top. Curr. Chem.  2006,  263:  107 

<A NAME="RZ04608SS-1B">1b</A> Sibi MP. Manyem S. Zimmerman J. Chem. Rev.  2003,  103:  3263 

<A NAME="RZ04608SS-1C">1c</A> Bar G. Parsons A. Chem. Soc. Rev.  2003,  32:  251 

<A NAME="RZ04608SS-1D">1d</A> Sibi MP. Rheault TR. In Radicals in Organic Synthesis   Vol. 1:  Renaud P. Sibi MP. VCH; Weinheim: 2001.  p.461-478  

<A NAME="RZ04608SS-1E">1e</A> Sibi MP. Porter NA. Acc. Chem. Res.  1999,  32:  163 

For a recent organocatalytic approach, see:

<A NAME="RZ04608SS-2A">2a</A> Sibi MP. Hasegawa M. J. Am. Chem. Soc.  2007,  129:  4124 

<A NAME="RZ04608SS-2B">2b</A> Beeson TD. Mastrachhio A. Hong J.-B. Ashton K. MacMillan DWC. Science  2007,  316:  582 

<A NAME="RZ04608SS-3">3</A> For a review, see: Srikanth GSC. Castle SL. Tetrahedron  2005,  61:  10377 

<A NAME="RZ04608SS-4">4</A> For a review, see: Miyabe H. Takemoto Y. Chem. Eur. J.  2007,  13:  7280 

<A NAME="RZ04608SS-5">5</A> Nishida M. Hayashi H. Nishida A. Kawahara N. Chem. Commun.  1996,  579 

For diastereoselective acrylate additions, see, for example:

<A NAME="RZ04608SS-6A">6a</A> Nishida N. Ueyama E. Hayashi H. Ohtake Y. Yamaura Y. Yanaginuma E. Yonemitsu O. Nishida A. Kawahara N. J. Am. Chem. Soc.  1994,  116:  6455 

<A NAME="RZ04608SS-6B">6b</A> Enholm EJ. Cottone JS. Allais R. Org. Lett.  2001,  3:  145 

<A NAME="RZ04608SS-6C">6c</A> Enholm EJ. Cottone JS. Org. Lett.  2001,  3:  3959 

<A NAME="RZ04608SS-7A">7a</A> Zahouily M. Journet M. Malacria M. Synlett  1994,  366 

<A NAME="RZ04608SS-7B">7b</A> Keum G. Kang SB. Kim Y. Lee E. Org. Lett.  2004,  6:  1895 

<A NAME="RZ04608SS-8">8</A> Dressel M. Bach T. Org. Lett.  2006,  8:  3145 

<A NAME="RZ04608SS-9">9</A> For other work related to hydrogen-bond-mediated enantioselectivity in radical reactions, see: Cho DH. Jang DO. Chem. Commun.  2006,  5045 

For radical reactions, see:

<A NAME="RZ04608SS-10A">10a</A> Aechtner T. Dressel M. Bach T. Angew. Chem. Int. Ed.  2004,  43:  5849 

<A NAME="RZ04608SS-10B">10b</A> Dressel M. Aechtner T. Bach T. Synthesis  2006,  2206 

For selected applications in photochemical reactions, see:

<A NAME="RZ04608SS-11A">11a</A> Bach T. Bergmann H. Harms K. Angew. Chem. Int. Ed.  2000,  39:  2302 

<A NAME="RZ04608SS-11B">11b</A> Bach T. Bergmann H. J. Am. Chem. Soc.  2000,  122:  11525 

<A NAME="RZ04608SS-11C">11c</A> Bach T. Bergmann H. Harms K. Org. Lett.  2001,  3:  601 

<A NAME="RZ04608SS-11D">11d</A> Bach T. Bergmann H. Grosch B. Harms K. J. Am. Chem. Soc.  2002,  124:  7982 

<A NAME="RZ04608SS-11E">11e</A> Grosch B. Orlebar CN. Herdtweck E. Kaneda M. Wada T. Inoue Y. Bach T. Chem. Eur. J.  2004,  10:  2179 

<A NAME="RZ04608SS-12">12</A> Aparicio-Martínez S. Hall KR. Balbuena PB. J. Phys. Chem. A  2006,  110:  9183 

<A NAME="RZ04608SS-13">13</A> Patrick TB. Wu T.-T. J. Org. Chem.  1978,  43:  1506