Synthesis of Enantiomerically Pure (4S)-2-Alken-4-olides via (2S)-1-Phenylsulfonyl-2-alkanols
Reduction of 1-chloro-3-phenylsulfonyl-2-propanone with baker's yeast, followed by epoxidation and alkylation with Grignard reagents, yields enantiomerically pure (2S)-2-phenylsulfonyl-2-alkanols, which are converted into (4S)-2-alken-4-olides in 100perce
Tanikaga, Rikuhei,Hosoya, Ken,Kaji, Aritsune
p. 389 - 390
(2007/10/02)
Reactions of (2S)-1-Arenesulfonyl-2-alkanol Dianions with Aldehydes. Application to the Synthesis of Enantiomerically Pure (3S)-1-Alken-3-ols and (2E,4S)-4-hydroxy-2-alkenenitriles
Enantiomerically pure (2S)-1-arenesulfonyl-2-alkanols (1) were prepared by yeast reduction of 1-arenesulfonyl-3-chloro-2-propanones, followed by epoxydation and alkylation.Reaction of dianions of 1 with aldehydes occurred at the pro(R) position of C(1) to give 1,3-diols, which were converted to (3S)-1-alken-3-ols or (2E,4S)-4-hydroxy-2-alkenenitriles in 100percent e.e.
Tanikaga, Rikuhei,Hosoya, Ken,Kaji, Aritsune
p. 829 - 832
(2007/10/02)
Ready Nucleophilic Ring Opening of β-Epoxy-sulphone, -sulphoxide, and -ester with Grignard Reagents
Treatment of β-epoxy-sulphone, -sulphoxide, and -ester with Grignard reagents and copper(I) iodide in diethyl ether-tetrahydrofuran at low temperature leads to rapid ring opening without loss of chirality.
Tanikaga, Rikuhei,Hosoya, Ken,Kaji, Aritsune
p. 836 - 837
(2007/10/02)
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