4-Substituted Prolyl Sulfonamides as Enantioselective Organocatalysts for Aldol Reactions

Evagelos Bellis; Konstantina Vasilatou; George Kokotos

doi:10.1055/s-2005-870026

PAPER

4-Substituted Prolyl Sulfonamides as Enantioselective Organocatalysts for Aldol Reactions

Evagelos Bellis, Konstantina Vasilatou, George Kokotos*
Laboratory of Organic Chemistry, Department of Chemistry, University of Athens, Panepistimiopolis, Athens 15771, Greece
Fax: +30(210)7274761; e-Mail: gkokotos@cc.uoa.gr;

Abstract

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Abstract

A series of prolyl and 4-substituted prolyl sulfonamides were prepared and were evaluated as organocatalysts of asymmetric aldol reaction. Using prolyl methanesulfonamide, 4-benzyloxy-prolyl methanesulfonamide and toluenesulfonamide and 4-hydroxyprolyl toluenesulfonamide the aldol product was obtained in much higher enantiomeric excess (ee) in comparison to that observed using proline itself. In addition, these new catalysts may be used in lower sub-stoichiometric amounts than proline, because of their improved solubility in organic solvents.

Key words

aldol reactions - amino acids - asymmetric catalysis - catalysis - sulfonamides

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References

For reviews see:

<A NAME="RT00505SS-1A">1a</A> Dalko PI. Moisan L. Angew. Chem. Int. Ed. 2001, 40: 3726

<A NAME="RT00505SS-1B">1b</A> Dalko PI. Moisan L. Angew. Chem. Int. Ed. 2004, 43: 5138

For reviews see:

<A NAME="RT00505SS-2A">2a</A> List B. Synlett 2001, 1675

<A NAME="RT00505SS-2B">2b</A> List B. Tetrahedron 2002, 58: 5573

<A NAME="RT00505SS-2C">2c</A> Paraskar AS. Synlett 2003, 582

<A NAME="RT00505SS-3A">3a</A> Hajos ZG. Parrish DR. J. Org. Chem. 1974, 39: 1615

<A NAME="RT00505SS-3B">3b</A> Eder U. Sauer G. Wiechert R. Angew. Chem. Int. Ed. Engl. 1971, 10: 496

<A NAME="RT00505SS-4">4</A> List B. Lerner RA. Barbas CF. J. Am. Chem. Soc. 2000, 122: 2395

<A NAME="RT00505SS-5A">5a</A> List B. Pojarliev P. Martin HJ. Org. Lett. 2001, 3: 2423

<A NAME="RT00505SS-5B">5b</A> Betancort JM. Sakthivel K. Thayumanavan R. Barbas CF. Tetrahedron Lett. 2001, 42: 4441

<A NAME="RT00505SS-5C">5c</A> Enders D. Seki A. Synlett 2002, 26

<A NAME="RT00505SS-6A">6a</A> List B. Pojarliev P. Biller WT. Martin HJ. J. Am. Chem. Soc. 2002, 124: 827

<A NAME="RT00505SS-6B">6b</A> Córdova A. Barbas CF. Tetrahedron Lett. 2003, 44: 1923

<A NAME="RT00505SS-6C">6c</A> Hayashi Y. Tsuboi W. Shoji M. Suzuki N. J. Am. Chem. Soc. 2003, 125: 11208

<A NAME="RT00505SS-6D">6d</A> Córdova A. Chem.-Eur. J. 2004, 10: 1987

<A NAME="RT00505SS-6E">6e</A> For a review see: Córdova A. Acc. Chem. Res. 2004, 37: 102

<A NAME="RT00505SS-7A">7a</A> List B. J. Am. Chem. Soc. 2002, 124: 5656

<A NAME="RT00505SS-7B">7b</A> Kumaragurubaran N. Juhl K. Zuang W. Bøgevig A. Jørgensen KA. J. Am. Chem. Soc. 2002, 124: 6254

<A NAME="RT00505SS-7C">7c</A> For a review see: Duthaler RO. Angew. Chem. Int. Ed. 2003, 42: 975

<A NAME="RT00505SS-8A">8a</A> Zhong G. Angew. Chem. Int. Ed. 2003, 42: 4247

<A NAME="RT00505SS-8B">8b</A> Brown SP. Brochu MP. Sinz CJ. MacMillan DWC. J. Am. Chem. Soc. 2003, 125: 10808

<A NAME="RT00505SS-8C">8c</A> For a review see: Merino P. Tejero T. Angew. Chem. Int. Ed. 2004, 43: 2995

Presented in part at the 1^st Hellenic Symposium on Organic Synthesis; Athens, 4-6 November, 2004; Abstracts p. 41.

<A NAME="RT00505SS-10">10</A> Patani GA. LaVoie EJ. Chem. Rev. 1996, 96: 3147

<A NAME="RT00505SS-11A">11a</A> Torii H. Nakadai M. Ishihara K. Saito S. Yamamoto H. Angew. Chem. Int. Ed. 2004, 43: 1983

<A NAME="RT00505SS-11B">11b</A> Yamamoto Y. Momiyama N. Yamamoto H. J. Am. Chem. Soc. 2004, 126: 5962

<A NAME="RT00505SS-12">12</A> Cobb AJA. Shaw DM. Ley SV. Synlett 2004, 558

<A NAME="RT00505SS-13">13</A> Cobb AJA. Shaw DM. Longbottom DA. Gold JB. Ley SV. Org. Biomol. Chem. 2005, 3: 84

<A NAME="RT00505SS-14">14</A> Hartikka A. Arvidsson PI. Tetrahedron: Asymmetry 2004, 15: 1831

<A NAME="RT00505SS-15">15</A> Berkessel A. Koch B. Lex J. Adv. Synth. Catal. 2004, 346: 1141

<A NAME="RT00505SS-16">16</A> Dowell RI. Hadley EM. J. Med. Chem. 1992, 35: 800

<A NAME="RT00505SS-17">17</A> Kokotos G. Synthesis 1990, 299

<A NAME="RT00505SS-18">18</A> Kokotos G. Markidis T. Constantinou-Kokotou V. Synthesis 1996, 1223

<A NAME="RT00505SS-19">19</A> Sakthivel K. Notz W. Bui T. Barbas CF. J. Am. Chem. Soc. 2001, 123: 5260

<A NAME="RT00505SS-20A">20a</A> Bahmanyar S. Houk KN. J. Am. Chem. Soc. 2001, 123: 12911

<A NAME="RT00505SS-20B">20b</A> List B. Hoang L. Martin HJ. Proc. Natl. Acad. Sci. U.S.A. 2004, 101: 5839

<A NAME="RT00505SS-20C">20c</A> List B. Acc. Chem. Res. 2004, 37: 548

<A NAME="RT00505SS-20D">20d</A> Allemann C. Gordillo R. Clemente FR. Cheong PH.-Y. Houk KN. Acc. Chem. Res. 2004, 37: 558

<A NAME="RT00505SS-21">21</A> Afonso CA. Synth. Commun. 1998, 28: 261