Synthesis and application of oxadiazines as chiral ligands for the enantioselective addition of diethylzinc to aldehydes
MA Dean, SR Hitchcock
Index: Dean, Melissa A.; Hitchcock, Shawn R. Tetrahedron Asymmetry, 2010 , vol. 21, # 20 p. 2471 - 2478
Full Text: HTML
Citation Number: 7
Abstract
A series of oxadiazines derived from l-phenylalanine bearing phenolic substituents have been synthesized in a multistep, one pot process. This process involves the reaction of a mixed anhydride with a β-hydrazino alcohol, methanesulfonylation of the alcohol moiety, and base induced cyclization. The resultant oxadiazines were employed in the asymmetric addition of diethylzinc to aldehydes.
Related Articles:
Transforming rhinacanthin analogues from potent anticancer agents into potent antimalarial agents
[Kongkathip, Ngampong; Pradidphol, Narathip; Hasitapan, Komkrit; Grigg, Ronald; Kao, Wei-Chun; Hunte, Carola; Fisher, Nicholas; Warman, Ashley J.; Biagini, Giancarlo A.; Kongsaeree, Palangpon; Chuawong, Pitak; Kongkathip, Boonsong Journal of Medicinal Chemistry, 2010 , vol. 53, # 3 p. 1211 - 1221]
Direct displacement of alkoxy groups of vinylogous esters by Grignard reagents
[Brockway, Anthony J.; Gonzalez-Lopez, Marcos; Fettinger, James C.; Shaw, Jared T. Journal of Organic Chemistry, 2011 , vol. 76, # 9 p. 3515 - 3518]
1-Methoxyisobenzofuran: formation from 1, 3-dihydro-1, 1-dimethoxyisobenzofuran
[Makhlouf, Mansour A.; Rickborn, Bruce Journal of Organic Chemistry, 1981 , vol. 46, # 13 p. 2734 - 2739]