Stereochemistry of sulfur-lithium and tin-lithium exchange reactions of functionalized cyclopropanes

Tanaka, Kazuhiko; Minami, Koichiro; Funaki, I.; Suzuki, Hitomi

doi:10.1016/s0040-4039(00)94684-7

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-Buty•-2-[•-(2•4•6-trimethy•benzenesu•f•ny•amin•)-ethy•]-cy1

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Cited by 22 publications

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“…HRMS (M)÷; Calcd for C24H37NO6S: 467.2342; Found: 467.2339 amu. (14). Purification by flash column chromatography using hexane-EtOAc (7 6.93+6.94 (2s, 2H, 3, 5-C6H2); Igc NMR (CDCls) 8 14.0, 20.8, 22.4, 23.0, 23.1, 24.0, 29.2, 31.0, 31.3, 31.6, 35.3, 35.5, 36.7, 50.3, 61.1, 61.6, 131.9, 136.2, 138.4, 141.8, 167.0, 170.7; HRMS (M)+; Calcd for C29H47NO6S: 537.3124; Found: 537.3125 ainu.…”

Section: -Buty•-2-[•-(2•4•6-trimethy•benzenesu•f•ny•amin•)-ethy•]-cymentioning

confidence: 99%

Synthesis of functionalized cyclopropanes by MIRC reactions of aziridinyl-methylenemalonates

Funaki¹,

Bell²,

Thijs³

et al. 1996

Tetrahedron

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The synthesis of cyclopropane derivatives via a MIRC reaction of azidirinyl-methylenemalonates is described. In this way it is possible to introduce a hydrogen, a phenylthio, a tributylstannyl and an olefinic function at the cyclopropane ring, that further contains an alkylamino substituent, Addition of CuCN catalyzed Grignard reagents gave the most promising results. The diastereoselectivity was dependent on the aziridine nitrogen substituent and the bulkiness of the reagent.

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Section: -Buty•-2-[•-(2•4•6-trimethy•benzenesu•f•ny•amin•)-ethy•]-cymentioning

confidence: 99%