Literature DB >> 11674435

Effect of beta-Substituents on the Regioselectivity of the Diazomethane Ring Expansion of alpha-Methyl-alpha-methoxycyclobutanones to Cyclopentanones.

Lisa M. Reeder1, Louis S. Hegedus.   

Abstract

The ring expansion of 22 differently beta-substituted alpha-methyl-alpha-methoxycyclobutanones by diazomethane was studied. Migration of the less-substituted alpha-carbon was favored with the single exception of a very sterically hindered beta-benzyloxy beta-substituent.

Entities:  

Year:  1999        PMID： 11674435     DOI： 10.1021/jo990226o

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  2 in total

1.  General Methodologies Toward cis-Fused Quinone Sesquiterpenoids. Enantiospecific Synthesis of the epi-Ilimaquinone Core Featuring Sc-Catalyzed Ring Expansion.

Authors:  Hilan Z Kaplan; Victor L Rendina; Jason S Kingsbury
Journal:  Molecules       Date:  2017-06-24       Impact factor: 4.411

2.  Stereoselective Synthesis of trans-Decalin-Based Spirocarbocycles via Photocyclization of 1,2-Diketones.

Authors:  Sijia Chen; Zhongchao Zhang; Chongguo Jiang; Chunbo Zhao; Haojie Luo; Jun Huang; Zhen Yang
Journal:  ACS Omega       Date:  2021-07-13
  2 in total

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