康 · 学术 | Reaction of the Day No. 1177
2024-03-06
临床研究
Vitamin B12-Photocatalyzed Cyclopropanation of
Electron-Deficient Alkenes Using Dichloromethane as the Methylene SourceJohn Hayford G. Teye-Kau, Mayokun J.
Ayodele, and Spencer P. Pitre*Department of Chemistry, Oklahoma State
University, 107 Physical Sciences, Stillwater, OK 74078, USA—Angew Chem. Int. Ed., 2024,
DOI: 10.1002/anie.202316064Recommended by Shi Li_ MOCABSTRACT: A
vitamin B12-photocatalyzed strategy was reported for
the cyclopropanation of
electron-deficient alkenes using dichloromethane (CH2Cl2) as
the methylene source. The reaction has excellent functional group tolerance, is
highly chemoselective, and
the scope can be extended to other 1,1-dichloroalkanes for the preparation of D2-cyclopropyl and methyl-substituted
cyclopropyl adducts, all of which are important isosteres in medical chemistry.Background and this workMechanistic designSubstrate ScopeMechanistic studiesFormation
of the Co(I) oxidation state of Vitamin B12 and
the subsequent SN2-type nucleophilic substitution with CH2Cl2 toformintermediate I under reaction conditions.Formation
of •CH2Cl radicalsSummary and CommentsProf.
Spencer P. Pitre et
al developed
a practical and efficient Vitamin B12 photocatalyzed approach
for the cyclopropanation of
electron-deficient alkenes using CH2Cl2 as the methylene source. The
reaction works for a broad range of electron-deficient alkenes, proceeds in
high chemoselectivity, and
has increased functional group tolerance compared to other state-of-the-art
methods. This approach will be of great value to medicinal chemists for the late-stage
incorporation of cyclopropyl isosteres in pharmaceutically active compounds due
to the biocompatibility and water solubility of Vitamin B12.Spencer
P. Pitre教授等人在光照条件下以CH2Cl2作为亚甲基源，开发了一种高效实用的维生素B12催化的缺电子烯烃的环丙烷化反应。与其他先进的方法相比，该反应适用于广泛的缺电子烯烃，具有更高的化学选择性和官能团耐受性。由于维生素B12的生物相容性和水溶性，这是一种药物化学家在药物活性化合物中后期引入环丙基的好方法，具有重要的应用价值。
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