Scandium(III) Triflate as an Efficient and Recyclable Catalyst for Chemo­selective Conversion of Carbonyl Compounds to 1,3-Oxathiolanes

Abstract

A variety of carbonyl compounds can be easily and rapidly converted to the corresponding 1,3-oxathiolanes in the presence of a catalytic amount of scandium(III) triflate [Sc(OTf)₃] in CH₂Cl₂. After completion of the reaction, the catalyst can straightforwardly be recovered using standard methods. Moreover, by employing this protocol, chemoselective oxathioacetalization of aldehydes in the presence of ketones can be achieved.

heterocycles - protecting groups - acetals - - scandium - aldehydes - ketones - catalysis

References

<A NAME="RZ04003SS-1">1</A> Greene TW. Wuts PGM. Protective Groups in Organic Synthesis   3rd ed.:  Wiley; New York: 1999.  Chap. 4.

<A NAME="RZ04003SS-2A">2a</A> Fuji K. Ueda M. Fujita E. J. Chem. Soc., Chem. Commun.  1977,  814 

<A NAME="RZ04003SS-2B">2b</A> Fuji K. Ueda M. Sumi K. Kajiwara K. Fujita E. Iwashita T. Miura I. J. Org. Chem.  1985,  50:  657 

<A NAME="RZ04003SS-2C">2c</A> Fuji K. Ueda M. Sumi K. Fujita E. Tetrahedron Lett.  1981,  22:  2005 

<A NAME="RZ04003SS-2D">2d</A> Fuji K. Ueda M. Fujita E. J. Chem. Soc., Chem. Commun.  1983,  49 

<A NAME="RZ04003SS-3A">3a</A> Lynch JE. Eliel EL. J. Am. Chem. Soc.  1984,  106:  2943 

<A NAME="RZ04003SS-3B">3b</A> Eliel EL. Morris-Natschke S. J. Am. Chem. Soc.  1984,  106:  2937 

<A NAME="RZ04003SS-3C">3c</A> Frye SV. Eliel EL. Tetrahedron Lett.  1985,  26:  3907 

<A NAME="RZ04003SS-3D">3d</A> Eliel EL. Soai K. Tetrahedron Lett.  1981,  21:  2859 

<A NAME="RZ04003SS-4A">4a</A> Isobe M. Obeyama J. Funabashi Y. Goto T. Tetrahedron Lett.  1988,  29:  4773 

<A NAME="RZ04003SS-4B">4b</A> Utimoto K. Nakamura A. Matsubara S. J. Am. Chem. Soc.  1990,  112:  8189 

<A NAME="RZ04003SS-5">5</A> Ralls JW. Dodson RM. Riegel B. J. Am. Chem. Soc.  1949,  71:  3320 

<A NAME="RZ04003SS-6">6</A> Mondal E. Sahu PR. Khan AT. Synlett  2002,  463 

<A NAME="RZ04003SS-7">7</A> Djerssi C. Gorman M. J. Am. Chem. Soc.  1953,  75:  3704 

<A NAME="RZ04003SS-8">8</A> Wilson GE. Huang MG. Schloman WW. J. Org. Chem.  1968,  33:  2133 

<A NAME="RZ04003SS-9">9</A> Mondal E. Sahu PR. Bose G. Khan AT. Tetrahedron Lett.  2002,  43:  2843 

<A NAME="RZ04003SS-10">10</A> Ravindranathan T. Chavan SP. Dantale W. Tetrahedron Lett.  1995,  36:  2285 

<A NAME="RZ04003SS-11">11</A> Streinz L. Koutek B. Saman D. Coll. Czech. Chem. Commun.  1997,  62:  665 

<A NAME="RZ04003SS-12">12</A> Burczyk B. Kortylewicz Z. Synthesis  1982,  831 

<A NAME="RZ04003SS-13">13</A> Karimi B. Seradj H. Synlett  2000,  805 

<A NAME="RZ04003SS-14">14</A> Romo J. Rosenkranz G. Djerassi C. J. Am. Chem. Soc.  1951,  73:  4961 

<A NAME="RZ04003SS-15A">15a</A> For a review, see: Kobayashi S. Eur. J. Org. Chem.  1999,  1:  15 

<A NAME="RZ04003SS-15B">15b</A> See also: Kobayashi S. Sugiura M. Kitagawa H. Lam WW.-L. Chem. Rev.  2002,  102:  2227 

<A NAME="RZ04003SS-16">16</A> Kobayashi S. Synlett  1994,  689 

<A NAME="RZ04003SS-17">17</A> Crotti P. Bussol VD. Favero L. Psero M. J. Org. Chem.  1996,  61:  9548 

<A NAME="RZ04003SS-18">18</A> Kobayashi S. Hachiya I. Araki M. Ishitani H. Tetrahedron Lett.  1993,  34:  3755 

<A NAME="RZ04003SS-19">19</A> Kawada A. Mitamura S. Kobayashi S. Synlett  1994,  545 

<A NAME="RZ04003SS-20">20</A> Kobayashi S. Hachiya I. Ishitani H. Araki M. Synlett  1993,  472 

<A NAME="RZ04003SS-21">21</A> Kobayashi S. Moriwaki M. Hachiya I. J. Chem. Soc., Chem. Commun.  1995,  1527 

<A NAME="RZ04003SS-22">22</A> Eliel EL. J. Am. Chem. Soc.  1959,  81:  6087 

<A NAME="RZ04003SS-23">23</A> Marshall JR. Stevenson HA. J. Chem. Soc.  1959,  2360 

<A NAME="RZ04003SS-24">24</A> Eliel EL. Pilate LA. Badding VG. J. Am. Chem. Soc.  1962,  84:  2377