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
Full Text: HTML
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 ...
Related Articles:
Simple and efficient MW-assisted cleavage of acetals and ketals in pure water
[Procopio, Antonio; Gaspari, Marco; Nardi, Monica; Oliverio, Manuela; Tagarelli, Antonio; Sindona, Giovanni Tetrahedron Letters, 2007 , vol. 48, # 49 p. 8623 - 8627]
[El-Qisairi, Arab K; Qaseer, Hanan A Journal of Organometallic Chemistry, 2002 , vol. 659, # 1-2 p. 50 - 55]
Aerobic Oxidation of Vicinal Diols Catalyzed by an Anderson??Type Polyoxometalate,[IMo6O24] 5–
[Advanced Synthesis and Catalysis, , vol. 344, # 9 p. 1017 - 1021]
Aerobic Oxidation of Vicinal Diols Catalyzed by an Anderson??Type Polyoxometalate,[IMo6O24] 5–
[Advanced Synthesis and Catalysis, , vol. 344, # 9 p. 1017 - 1021]
Aqueous-phase hydrodeoxygenation of bio-derived phenols to cycloalkanes
[Journal of Catalysis, , vol. 280, # 1 p. 8 - 16]