Heterocycles p. 937 - 940 (1993)
Update date:2022-07-29
Topics:
Matsuki, Kenji
Inoue, Hirozumi
Ishida, Akihiko
Takeda, Mikio
Bicyclic-5-hydroxy-2-pyrrolidinones (2a-f) were synthesized with high enantioselectivity by the reduction of meso-cyclic-1,2-dicarboximides (1a-f) with lithium aluminum hydride (LiAlH4)-methanol(MeOH)-1,1-bi-2-naphthol complex (BINAL-H).Treatment of 2a-f with triethylsilane (Et3SiH) and trifluoroacetic acid (CF3CO2H) gave optically active 2-pyrrolidinones (3a-f) in quantitative yields.For the absolute configuration correlation, 2a-d were converted into known lactones (4a-d).
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Doi:10.1016/S0040-4020(01)97150-9
(1974)Doi:10.1016/S0957-4166(00)80366-3
(1993)Doi:10.1016/j.bmcl.2013.11.034
(2014)Doi:10.1055/s-1999-3684
(1999)Doi:10.1016/0223-5234(93)90123-V
(1993)Doi:10.1021/jo00076a006
(1993)
