2,5-Dioxopyrrolidin-1-yl (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl carbonate

Wang, Tong-jian; Fang, Hua; Cheng, Fang; Tang, Guo; Zhao, Yufen

doi:10.1107/s1600536806049774

Cited by 2 publications

(2 citation statements)

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“…For deoxynojirimicine and iminosugars, see: Asano et al (2000); Watson et al (2001). For chiral auxiliary (À)-menthyl, see: Wang et al (2006).…”

Section: Related Literaturementioning

confidence: 99%

“…All H atoms were refined isotropically. The absolute configuration was assigned from the use of the chiral auxiliary (-)-menthyl (Wang et al, 2006) as the starting material, whose stereo centres are not involved in the reaction. Owing to the absence of significant anomalous dispersion for data collected with the Mo radiation, 2332 measured Friedel pairs were merged.…”

Section: S3 Refinementmentioning

confidence: 99%

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(Z,1S,10aR)-(−)-Menthyl 1-hydroxy-1,2,3,5,6,7,10,10a-octahydropyrrolo[1,2-a]azocine-10a-carboxylate

et al. 2012

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The structure determination confirms the stereochemistry of the title compound, C 21 H 35 NO 3 , obtained as an intermediate in the enantioselective synthesis of deoxynojirimicine analogs. The system contains a pyrrolo[1,2- a ]azocine backbone, which was synthesized by a domino process involving a [2,3]-sigmatropic rearrangement. The incorporation of a chiral auxiliary (−)-menthyl, whose stereocentres are not involved during the synthesis, enables the assignation of absolute configuration. The crystal structure features O—H⋯O hydrogen bonds involving the hydroxy groups as donors and the carbonyl groups as acceptors, which link the molecules into chains running along [010].

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“…For deoxynojirimicine and iminosugars, see: Asano et al (2000); Watson et al (2001). For chiral auxiliary (À)-menthyl, see: Wang et al (2006).…”

Section: Related Literaturementioning

confidence: 99%

Section: S3 Refinementmentioning

confidence: 99%