1, 3-diol synthesis via controlled, radical-mediated C− H functionalization

K Chen, JM Richter, PS Baran

Index: Chen, Ke; Richter, Jeremy M.; Baran, Phil S. Journal of the American Chemical Society, 2008 , vol. 130, # 23 p. 7247 - 7249

Full Text: HTML

Citation Number: 106

Abstract

The invention of a method for the synthesis of 1, 3-diols from the corresponding alcohols is described, via controlled, radical-mediated C− H functionalization. The sequence described herein entails near quantitative conversion to the corresponding trifluoroethyl carbamate, followed by a variant of the Hofmann− Löffler− Freytag reaction, cyclization, and hydrolysis to provide the 1, 3-diols. In addition to the 10 examples presented herein, the syntheses of ...

Related Articles:

Synthesis of Oxazolidin??2??ones and Imidazolidin??2??ones Directly from 1, 3??Diols or 3??Amino Alcohols using Iodobenzene Dichloride and Sodium Azide

[He, Tian; Gao, Wen-Chao; Wang, Wei-Kun; Zhang, Chi Advanced Synthesis and Catalysis, 2014 , vol. 356, # 5 p. 1113 - 1118]

Synthetic applications of glycidic thiolesters. Regioselective reduction to 1, 3-diols and 2, 3-epoxy alcohols

[Liu, Hsing-Jang; Luo, Weide Canadian Journal of Chemistry, 1992 , vol. 70, p. 128 - 134]

The Proline??Catalyzed Asymmetric Amination of Branched Aldehydes

[Cronyn et al. Journal of the American Chemical Society, 1955 , vol. 77, p. 3031,3033]

A β-hydroxyethyl carbanion equivalent

[Klos, Andrew M.; Heintzelman, Geoffrey R.; Weinreb, Steven M. Journal of Organic Chemistry, 1997 , vol. 62, # 11 p. 3758 - 3761]

A new approach to the synthesis of 1-oxaspiro [4. n] alkanes and tetrahydrofurans by the 1, 5-CH insertion reaction of magnesium carbenoids

[Satoh, Tsuyoshi; Yasoshima, Tsukasa; Momochi, Hitoshi Tetrahedron Letters, 2012 , vol. 53, # 16 p. 2074 - 2077]

More Articles...