Molybdenum(VI) Dichloride Dioxide Catalyzed Synthesis of β-Keto Esters by C-H Insertion of Ethyl Diazoacetate into Aldehydes

Abstract

Synthesis of β-keto esters by condensing various aldehydes with ethyl diazoacetate is achieved by using molybdenum(VI) dichloride dioxide. Aromatic, aliphatic, and heterocyclic aldehydes are successfully condensed with ethyl diazoacetate to obtain corresponding β-keto esters in high yields at room temperature.

molybdenum - catalyst - β-keto esters - aldehydes - ethyl diazoacetate

References

<A NAME="RZ05008SS-1">1</A> Bellina F. Ciucci D. Rossi R. Vergamini P. Tetrahedron  1999,  55:  2103 

<A NAME="RZ05008SS-2">2</A> Benetti S. Romagnoli R. Risi CD. Spalluto G. Zanirato V. Chem. Rev.  1995,  95:  1065 

<A NAME="RZ05008SS-3">3</A> Wang CLJ. Salvino JM. Tetrahedron Lett.  1984,  25:  5243 

<A NAME="RZ05008SS-4">4</A> Gilbert JC. Kelly TA. Tetrahedron Lett.  1989,  30:  4193 

<A NAME="RZ05008SS-5">5</A> Urban E. Knühl G. Helmchen G. Tetrahedron  1995,  51:  13031 

<A NAME="RZ05008SS-6">6</A> Magriotis PA. Johnson F. J. Org. Chem.  1984,  49:  1460 

<A NAME="RZ05008SS-7">7</A> Benbakkar M. Baltas M. Gorrichon L. Gorrichon JP. Synth. Commun.  1989,  19:  3241 

<A NAME="RZ05008SS-8">8</A> Ward RS. Synthesis  1992,  719 

<A NAME="RZ05008SS-9">9</A> Doyle MP. McKervey MA. Ye T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds   Wiley; New York: 1998.  p.551 

<A NAME="RZ05008SS-10A">10a</A> Holmquist CR. Roskamp EJ. J. Org. Chem.  1989,  54:  3258 

<A NAME="RZ05008SS-10B">10b</A> Dudley ME. Morshed MM. Brennan CL. Islam MS. Ahmad MS. Atuu MR. Branstetter B. Hossain MM. J. Org. Chem.  2004,  69:  7599 

<A NAME="RZ05008SS-11">11</A> Yadav JS. Reddy BVS. Eeshwaraiah B. Reddy PN. Tetrahedron  2005,  61:  875 

<A NAME="RZ05008SS-12">12</A> Dhavale DD. Patil PN. Mali RS. J. Chem. Res., Synop.  1994,  152 

<A NAME="RZ05008SS-13">13</A> Sudrik SG. Balaji BS. Singh AP. Mitra RB. Sonawane HR. Synlett  1996,  369 

<A NAME="RZ05008SS-14">14</A> Bandgar BP. Pandit SS. Sadavarte VS. Green Chem.  2001,  3:  247 

<A NAME="RZ05008SS-15A">15a</A> Sanz R. Aguado R. Pedrosa MR. Arnaiz FJ. Synthesis  2002,  856 

<A NAME="RZ05008SS-15B">15b</A> Sanz R. Escribano J. Aguado R. Pedrosa MR. Arnaiz FJ. Synthesis  2004,  1629 

<A NAME="RZ05008SS-15C">15c</A> Sanz R. Escribano J. Fernandez Y. Aguado R. Pedrosa MR. Arnaiz FJ. Synlett  2005,  1389 

<A NAME="RZ05008SS-15D">15d</A> Chen CT. Kuo JH. Pawar VD. Munot YS. Weng SS. Ku CH. Liu CY. J. Org. Chem.  2005,  70:  1188 

<A NAME="RZ05008SS-15E">15e</A> Fernandes AC. Fernandes R. Romao CC. Royo B. Chem. Commun.  2005,  213 

<A NAME="RZ05008SS-15F">15f</A> Weng SS. Lin YD. Chen C.-T. Org. Lett.  2006,  8:  5633 

<A NAME="RZ05008SS-15G">15g</A> Sanz R. Escribano J. Pedrosa MR. Aguado R. Arnaiz FJ. Adv. Synth. Catal.  2007,  349:  713 

<A NAME="RZ05008SS-16">16</A> Jeyakumar K. Chand DK. Tetrahedron Lett.  2006,  47:  4573 

<A NAME="RZ05008SS-17">17</A> Jeyakumar K. Chand DK. Appl. Organomet. Chem.  2006,  20:  840 

<A NAME="RZ05008SS-18">18</A> Jeyakumar K. Chand DK. Synthesis  2008,  807 

<A NAME="RZ05008SS-19A">19a</A> Taylor MJ. Jirong W. Rickard CEF. Polyhedron  1993,  12:  1433 

<A NAME="RZ05008SS-19B">19b</A> Arnaiz FJ. Inorg. Synth.  1997,  31:  246 

<A NAME="RZ05008SS-19C">19c</A> Arnaiz FJ. Aguado R. Sanz-Aparicio J. Martinez-Ripoll M. Polyhedron  1994,  13:  2745 

<A NAME="RZ05008SS-20">20</A> Armarego WLF. Perrin D. Purification of Laboratory Chemicals   4th ed.:  Butterworth-Heinemann; Oxford: 2002. 

<A NAME="RZ05008SS-21A">21a</A> Balaji BS. Chanda BM. Tetrahedron  1998,  54:  13237 

<A NAME="RZ05008SS-21B">21b</A> Wierenga W. Skulnick HI. J. Org. Chem.  1979,  44:  310 

<A NAME="RZ05008SS-21C">21c</A> Hok S. Schore NE. J. Org. Chem.  2006,  71:  1736 

<A NAME="RZ05008SS-21D">21d</A> Ballini R. Fiorini D. Palmieri A. Tetrahedron Lett.  2004,  45:  7027 

<A NAME="RZ05008SS-21E">21e</A> Katritzky AR. Wang Z. Wang M. Wilkerson CR. Hall CD. Akhmedov NG. J. Org. Chem.  2004,  69:  6617