Journal of Organic Chemistry p. 4238 - 4242 (1992)
Update date:2022-08-03
Topics:
Nagao, Yoshimitsu
Nagase, Yunosuke
Kumagai, Toshio
Kuramoto, Yasuhiro
Kobayashi, Shigeaki
et al.
Alkylation of rac 3-substituted 4-acetoxyazetidin-2-one 4 with chiral tin(II) enolate 8 derived from 3-acetyl-(4S)-ethyl-1,3-thiazolidine-2-thione (ETT) (7) proceeded in a highly diastereoselective manner to give alkylated products 9, 10, and 11 in 42percent, 20percent, and 9percent yields, respectively, after chromatographic purification.Similar alkylation of rac-5 with 8 gave 16, 17, and 18 in 45percent, 29percent, and 5percent yields, respectively.Compound 9 was readily converted to 33, a chiral key intermediate for the synthesis of carbapenems.Analytical separation of rac-4 was effectively done with an HPLC technique employing a chiral column packed with A(S)MBC.
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