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Enantioselective Syntheses of Substituted ƒ×ƒ{ -Butyrolactones
Ernest L. Eliel, Xu Bai and Masaki Ohwa
Abstract. The previously described chiral 2-acyloxathianes 5(Scheme I) are used in two different enantioselective syntheses of g-butyrolactones. In one synthesis, Grignard addition, cleavage and reduction to carbinols RR'C(OH)CH2OH is followed by tosylation, malonate homologation, lactonization, and removal of the carbomethoxy group to give optically active g-lactones. A modification of this synthesis (Scheme I) leads to optically active a-methylene-g-lactones. In the second synthesis, reaction of a bromomagnesium enolate with ketones 5 leads to b-hydroxyesters, which, by appropriate sequences of reduction and cleavage (Scheme II) are converted to optically active a- or b-hydroxy-g-lactones.
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The Efficient Synthesis of the Optically Active £]-Hydroxyl-£^-butyrolactone Derivatives
Jin Xin Wang, Ying Li* , Chao Xin Zhang
National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000, P. R. China
Abstract. The optically active £]-hydroxyl-£^-butyrolactones were synthesized from nonchiral starting material by employing reductive cleavage reaction, sharpless asymmetric epoxidation and dihydroxylation, and Lewis acid-catalysed cyclization as key steps. This strategy can be used to prepare many chiral b-hydroxyl-g-butyrolactone analogues.
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