Enantioselektive Synthese von β-Aminosulfonen über azaanaloge Michael-Addition an Alkenylsulfone

作者: Dieter Enders , Stephan F. Müller , Gerhard Raabe

DOI: 10.1002/(SICI)1521-3757(19990115)111:1/2<212::AID-ANGE212>3.0.CO;2-E

关键词:

摘要: Ob SAMP oder RAMBO deren Enantiomere RAMP bzw. SAMBO als chirale Ammoniakaquivalente verwendet werden: Die asymmetrische Synthese von N-geschutzten β-Aminosulfonen 4 gelingt stets mit sehr hohen Enantiomerenuberschussen durch Addition eines Stickstoff-Nucleophils ((S)-1 (R,R,R)-2) an (E)-Alkenylsulfone 3 und anschliesende reduktive N-N-Spaltung zur Entfernung des chiralen Auxiliars.

参考文章(26)
Daniela Braghiroli, Rossella Avallone, Maria Di Bella, ASYMMETRIC SYNTHESIS OF (R)- AND (S)-2-PYRROLIDINEMETHANESULFONIC ACID Tetrahedron-asymmetry. ,vol. 8, pp. 2209- 2213 ,(1997) , 10.1016/S0957-4166(97)00196-1
Hideshi Nakamura, Houming Wu, Junichi Kobayashi, Masaki Kobayashi, Yasushi Ohizumi, Yoshimasa Hirata, Agelasidines: novel hypotaurocyamine derivatives from the Okinawan sea sponge Agelas nakamurai Hoshino Journal of Organic Chemistry. ,vol. 50, pp. 2494- 2497 ,(1985) , 10.1021/JO00214A017
Jesús de Blas, Juan C. Carretero, Esteban Domínguez, Stereoselective approach to optically pure syn 2-amino alcohol derivatives Tetrahedron Letters. ,vol. 35, pp. 4603- 4606 ,(1994) , 10.1016/S0040-4039(00)60741-4
Nigel S. Simpkins, The chemistry of vinyl sulphones Tetrahedron. ,vol. 46, pp. 6951- 6984 ,(1990) , 10.1016/S0040-4020(01)87882-0
Yoshiyasu Ichikawa, First synthesis of agelasidine A Tetrahedron Letters. ,vol. 29, pp. 4957- 4958 ,(1988) , 10.1016/S0040-4039(00)80651-6
J-C. Wu, T. Pathak, W. Tong, J-M. Vial, G. Remaud, J. Chattopadhyaya, New syntheses of 2',3'-dideoxy-2',3'-di-substituted & -2'-mono-substituted uridines & adenosines by michael addition reactions Tetrahedron. ,vol. 44, pp. 6705- 6722 ,(1988) , 10.1016/S0040-4020(01)90111-5
Henry. Feuer, Frank. Brown, Chemistry of hydrazides. X. The reduction of cyclic and acyclic hydrazides with diborane The Journal of Organic Chemistry. ,vol. 35, pp. 1468- 1471 ,(1970) , 10.1021/JO00830A045