A cleavable linker strategy for optimising enolate alkylation reactions of a polymer-supported Evans' oxazolidin-2-one
作者： Rachel Green , Andrew T. Merritt , Steven D. Bull
DOI: 10.1039/B713966G
关键词:
摘要: A cleavable linker strategy has been used to optimise the enolate alkylation reactions of a recyclable L-tyrosine derived polymer-supported oxazolidin-2-one for asymmetric synthesis series chiral α-alkyl acids.
rsc.org
bath.ac.uk
sci-hub.se 参考文章(13)
David A. Evans, Thomas C. Britton, Jon A. Ellman, Contrasteric carboximide hydrolysis with lithium hydroperoxide Tetrahedron Letters. ,vol. 28, pp. 6141- 6144 ,(1987) , 10.1016/S0040-4039(00)61830-0
Steven M. Allin, Cara A. Johnson, Andreas Timm, Reinvestigation of a polymer-supported chiral auxiliary derived from serine Tetrahedron Letters. ,vol. 46, pp. 2495- 2497 ,(2005) , 10.1016/J.TETLET.2005.02.024
Tomoya Kotake, S Rajesh, Yoshio Hayashi, Yoshie Mukai, Mitsuhiro Ueda, Tooru Kimura, Yoshiaki Kiso, A new polymer-supported Evans-type chiral auxiliary derived from α-hydroxy-β-amino acid, phenylnorstatine: synthesis and application in solid-phase asymmetric alkylation reactions Tetrahedron Letters. ,vol. 45, pp. 3651- 3654 ,(2004) , 10.1016/J.TETLET.2004.03.043
Steven D. Bull, Stephen G. Davies, Simon Jones, Hitesh J. Sanganee, Asymmetric alkylations using SuperQuat auxiliaries—an investigation into the synthesis and stability of enolates derived from 5,5-disubstituted oxazolidin-2-ones Journal of The Chemical Society-perkin Transactions 1. pp. 387- 398 ,(1999) , 10.1039/A809715A
Steven M. Allin, Stephen J. Shuttleworth, THE PREPARATION AND FIRST APPLICATION OF A POLYMER-SUPPORTED EVANS OXAZOLIDINONE Tetrahedron Letters. ,vol. 37, pp. 8023- 8026 ,(1996) , 10.1016/0040-4039(96)01815-1
Sean P Bew, Steven D Bull, Stephen G Davies, Edward D Savory, David J Watkin, Rearrangements and racemisation during the synthesis of l-serine derived oxazolidin-2-ones Tetrahedron. ,vol. 58, pp. 9387- 9401 ,(2002) , 10.1016/S0040-4020(02)01223-1
Sean P Bew, Steven D Bull, Stephen G Davies, Polymer supported oxazolidin-2-ones derived from l-serine—a cautionary tale Tetrahedron Letters. ,vol. 41, pp. 7577- 7581 ,(2000) , 10.1016/S0040-4039(00)01301-0
Derrick L. J. Clive, K. S. Keshava Murthy, Andrew G. H. Wee, J. Siva Prasad, Gil V. J. Da Silva, Marek Majewski, Paul C. Anderson, Claire F. Evans, Richard D. Haugen, Total synthesis of both (+)-compactin and (+)-mevinolin : a general strategy based on the use of a special titanium reagent for dicarbonyl coupling Journal of the American Chemical Society. ,vol. 112, pp. 3018- 3028 ,(1990) , 10.1021/JA00164A024
Tomoya Kotake, Yoshio Hayashi, S. Rajesh, Yoshie Mukai, Yuka Takiguchi, Tooru Kimura, Yoshiaki Kiso, Design and synthesis of a new polymer-supported Evans-type oxazolidinone: an efficient chiral auxiliary in the solid-phase asymmetric alkylation reactions Tetrahedron. ,vol. 61, pp. 3819- 3833 ,(2005) , 10.1016/J.TET.2005.01.135
Rachel Green, Piers J.M. Taylor, Steven D. Bull, Tony D. James, Mary F. Mahon, Andy T. Merritt, A practical synthesis of enantiopure (S)-4-(4-hydroxybenzyl)-oxazolidin-2-one Tetrahedron-asymmetry. ,vol. 14, pp. 2619- 2623 ,(2003) , 10.1016/S0957-4166(03)00482-8