Unexpected Temperature, Time and Solvent Effects in the Catalytic ­Asymmetric aza-Diels-Alder Reaction of an Ethyl Glyoxylate-derived N-Aryl Imine with Danishefsky’s Diene Catalysed by a BINOL-Zinc Complex

Abstract:

The catalytic asymmetric aza-Diels-Alder reaction of an ethyl glyoxylate-derived N-aryl imine with Danishefsky’s diene using a BINOL-zinc complex provides the corresponding cycloadduct with moderate to high enantioselectivity, depending on the solvent, temperature and reaction time.

heterodienophile - Diels-Alder reaction - asymmetric induction - BINOL-zinc

References

<A NAME="RD28403ST-1A">1a</A> Baliah V. Jeyaraman R. Chandrasekaran L. Chem. Rev.  1983,  83:  379 

<A NAME="RD28403ST-1B">1b</A> Jørgensen KA. Angew Chem. Int. Ed.  2000,  39:  3559 

<A NAME="RD28403ST-1C">1c</A> Buonora P. Olsen J.-C. Oh T. Tetrahedron  2001,  57:  6099 

<A NAME="RD28403ST-2">2</A> Hattori K. Yamamoto H. Tetrahedron  1993,  49:  1749 

<A NAME="RD28403ST-3A">3a</A> Ishitani H. Kobayashi S. Tetrahedron Lett.  1996,  37:  7357 

<A NAME="RD28403ST-3B">3b</A> Kobayashi S. Komiyama S. Ishitami H. Angew. Chem. Int. Ed.  1998,  37:  979 

<A NAME="RD28403ST-4A">4a</A> Yao S. Johannsen M. Hazell RG. Jorgensen KA. Angew. Chem. Int. Ed.  1998,  37:  3121 

<A NAME="RD28403ST-4B">4b</A> Kobayashi S. Kusakabe K. Komiyama S. Ishitami H. J. Org. Chem.  1999,  64:  4220 

<A NAME="RD28403ST-4C">4c</A> Yao S. Saaby S. Hazell RG. Jorgensen KA. Chem.-Eur. J.  2000,  6:  2435 

<A NAME="RD28403ST-4D">4d</A> Kobayashi S. Kusakabe K. Ishitani H. Org. Lett.  2000,  2:  1225 

<A NAME="RD28403ST-4E">4e</A> Josephsohn NS. Snapper ML. Hoveyda AH. J. Am. Chem. Soc.  2003,  125:  4018 

<A NAME="RD28403ST-4F">4f</A> Bromidge S. Wilson PC. Whiting A. Tetrahedron Lett.  1998,  39:  8905 

<A NAME="RD28403ST-4G">4g</A> Bundu A. Guillarme S. Hannan J. Wan H. Whiting A. Tetrahedron Lett.  2003,  44:  7849 

<A NAME="RD28403ST-5">5</A> Rosini C. Franzini L. Raffaelli A. Salvadori P. Synthesis  1992,  503 

<A NAME="RD28403ST-6">6</A> Danishefsky SJ. Kitahara T. J. Am. Chem. Soc.  1974,  96:  7807 

<A NAME="RD28403ST-7">7</A> Sakane S. Maruaka K. Yamamoto H. Tetrahedron  1986,  43:  2203 

<A NAME="RD28403ST-8">8</A> Corminboeuf O. Renaud P. Org. Lett.  2002,  4:  1735 

<A NAME="RD28403ST-9A">9a</A> Du H. Long J. Hu J. Li X. Ding K. Org. Lett.  2002,  4:  4349 

<A NAME="RD28403ST-9B">9b</A> Du H. Ding K. Org. Lett.  2003,  5:  1091 

<A NAME="RD28403ST-10">10</A> Muchow G. Vannoorenberghe Y. Buono G. Tetrahedron Lett.  1987,  28:  6163 

<A NAME="RD28403ST-11A">11a</A> Brunel JM. Pardigon O. Faure B. Buono G. J. Chem Soc., Chem. Commun.  1992,  287 

<A NAME="RD28403ST-11B">11b</A> Brunel JM. Buono G. Synlett  1999,  177 

<A NAME="RD28403ST-11C">11c</A> Brunel JM. Chiodi O. Faure B. Buono G. J. Organomet. Chem.  1997,  529:  285