A new resolution procedure for the preparation of both (R)-(+)-and (S)-(-)-4-tert-butoxycyclopent-2-enone from racemic 4-tert-butoxycyclopent-2-enone and conversion …
…, RK Haynes, MD Ironside, S Kremmydas…
Index: Eschler, Bart M.; Haynes, Richard K.; Ironside, Michael D.; Kremmydas, Steve; Ridley, Damon D.; Hambley, Trevor W. Journal of Organic Chemistry, 1991 , vol. 56, # 15 p. 4760 - 4766
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Citation Number: 25
Abstract
(1S)-(-)-lO-Mercaptoibomeol undergoes conjugate addition to (f)-4tert-butoxycyclopent-2- enone in methanol containing N, N,","-tetramethylethylenediamine to give a 1: l mixture of diastereomers of 3-tert-butoxy-4-[[(exo-2'-hydroxy-7', 7'-dimethylbicyclo [2.2. 1] heptanyl) methyl] thio] cyclopentanone in 93-95% yield. The mixture is converted by m- chloroperbenzoic acid into the corresponding sulfoxide mixture. The (3R, 4R, R~)- ...
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