Some aspects of intramolecular carbocyclization of methyl (2 E )-3-[(1 S ,2 R ,5 R )-2-({[ tert -butyl(dimethyl)-silyl]oxy}methyl)-5-(trimethylsilyl)cyclopent-3-en-1-yl]prop-2-enoate and its derivatives

A. M. Gimazetdinov; A. Z. Al’mukhametov; L. V. Spirikhin; M. S. Miftakhov

doi:10.1134/S1070428017060057

Some aspects of intramolecular carbocyclization of methyl (2E)-3-[(1S,2R,5R)-2-({[tert-butyl(dimethyl)-silyl]oxy}methyl)-5-(trimethylsilyl)cyclopent-3-en-1-yl]prop-2-enoate and its derivatives

作者: Gimazetdinov A.M.¹, Al’mukhametov A.Z.¹, Spirikhin L.V.¹, Miftakhov M.S.¹
隶属关系:
1. Ufa Institute of Chemistry
期: 卷 53, 编号 6 (2017)
页面: 836-845
栏目: Article
URL: https://journal-vniispk.ru/1070-4280/article/view/216328
DOI: https://doi.org/10.1134/S1070428017060057
ID: 216328

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Treatment of methyl (2E)-3-[(1S,2R,5R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-(trimethylsilyl) cyclopent-3-en-1-yl]prop-2-enoate with Bu₄NF in THF resulted in intramolecular cyclization with formation of bicyclo[3.1.0]hexene structure. Possible ways of cyclopropane ring closure were discussed. Methyl (2E)-3-[(1R,4R,5S)-5-formyl-4-(trimethylsilyl)cyclopent-2-en-1-yl]prop-2-enoate failed to undergo intramolecular Baylis–Hillman reaction.