Tetrahedron

Stereoselective functionalisation of SuperQuat enamides: asymmetric synthesis of homochiral 1, 2-diols and α-benzyloxy carbonyl compounds

…, PM Roberts, H Rodriguez-Solla, C O'Leary-Steele…

Index: Aciro, Caroline; Davies, Stephen G.; Garner, A. Christopher; Ishii, Yutaka; Key, Min-Suk; Ling, Kenneth B.; Prasad, R. Shyam; Roberts, Paul M.; Rodriguez-Solla, Humberto; O'Leary-Steele, Catherine; Russell, Angela J.; Sanganee, Hitesh J.; Savory, Edward D.; Smith, Andrew D.; Thomson, James E. Tetrahedron, 2008 , vol. 64, # 39 p. 9320 - 9344

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Citation Number: 25

Abstract

Homochiral (E)-and (Z)-enamides derived from SuperQuat (S)-4-phenyl-5, 5-dimethyl- oxazolidin-2-one undergo highly diastereoselective epoxidation upon treatment with dimethyldioxirane. Subsequent epoxide opening with meta-chlorobenzoic acid proceeds via a stereoselective SN1-type process, with retention of configuration, to give the corresponding 1′-m-chlorobenzoyl-2′-hydroxy derivatives. Treatment of the SuperQuat ...