Chiral linker 5: scope and limitations of arylsubstituted m-hydrobenzoins as solid supported open chain chiral auxiliaries for diastereoselective syntheses
作者： Joachim Broeker , Max Knollmueller , Peter Gaertner
DOI: 10.1016/J.TETASY.2009.02.004
关键词:
摘要: Abstract The applicability of five aryl substituted m-hydrobenzoin ethers already tested in the L-Selectride® mediated stereoselective reduction phenylglyoxylates as open chain chiral auxiliaries was further investigated via α-alkylation propionates, addition n-BuZnCl to and Diels–Alder reaction acrylates with cyclopentadiene model reactions. As up 90% de could be achieved solution phase, two optimized auxiliary structures were immobilized on commercially available Wang-resin applied a reusable solid supported same type
elsevier.com
sci-hub.se 参考文章(93)
Herbert Waldmann, Johann Hermann Wolfgang Mulzer, Organic Synthesis Highlights ,(1990)
Marc Larcheveque, Eliana Ignatova, Thérèse Cuvigny, Asymmetric synthesis of α-substituted ketones and acids via chiral N,N- substituted amides Tetrahedron Letters. ,vol. 19, pp. 3961- 3964 ,(1978) , 10.1016/S0040-4039(01)95111-1
Marc Larcheveque, Eliana Ignatova, Thérèse Cuvigny, Asymmetric alkylation of chiral N,N-disubstituted amides Journal of Organometallic Chemistry. ,vol. 177, pp. 5- 15 ,(1979) , 10.1016/S0022-328X(00)92326-X
David Tanner, Carin Birgersson, Adolf Gogoll, Kristina Luthman, On the use of C2-symmetric aziridines as chiral auxiliaries Tetrahedron. ,vol. 50, pp. 9797- 9824 ,(1994) , 10.1016/S0040-4020(01)85546-0
Pelayo Camps, Mercè Font-Bardia, Sı́lvia Giménez, Francesc Pérez, Xavier Solans, Núria Soldevilla, (R)- and (S)-3-Hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone as chiral auxiliaries in Diels–Alder reactions Tetrahedron-asymmetry. ,vol. 10, pp. 3123- 3138 ,(1999) , 10.1016/S0957-4166(99)00267-0
D.A. Evans, J.M. Takacs, Enantioselective alkylation of chiral enolates Tetrahedron Letters. ,vol. 21, pp. 4233- 4236 ,(1980) , 10.1016/S0040-4039(00)92870-3
Thuy X.H. Le, Jacqueline C. Bussolari, William V. Murray, 2,5-Diketopiperazines, new chiral auxiliaries for asymmetric Diels-Alder reactions Tetrahedron Letters. ,vol. 38, pp. 3849- 3852 ,(1997) , 10.1016/S0040-4039(97)00769-7
G. Boireau, A. Deberly, D. Abenhaïm, Synthese D'α-hydroxyacides optiquement actifs par addition d'organozinciques sur le phenylglyoxalate de (−) menthyle Tetrahedron. ,vol. 45, pp. 5837- 5844 ,(1989) , 10.1016/S0040-4020(01)89110-9
Joachim Broeker, Max Knollmueller, Peter Gaertner, Chiral linker. Part 3: Synthesis and evaluation of aryl substituted m-hydrobenzoins as solid supported open chain chiral auxiliaries for the diastereoselective reduction of α-keto esters Tetrahedron-asymmetry. ,vol. 17, pp. 2413- 2429 ,(2006) , 10.1016/J.TETASY.2006.08.017
Patrizia Scafato, Laura Leo, Stefano Superchi, Carlo Rosini, Monobenzylethers of (R, R)-1,2-diphenylethane-1,2-diol as a possible alternative to cyclohexyl-based chiral auxiliaries in the stereoselective reduction of α-ketoesters Tetrahedron. ,vol. 58, pp. 153- 159 ,(2002) , 10.1016/S0040-4020(01)01117-6