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A Short and Efficient Synthesis of ( R , R )-2-Methylcyclopropanecarboxylic Acid

✍ Scribed by Delhaye, Laurent; Merschaert, Alain; Delbeke, Pieter; Briône, Willy


Book ID
126216751
Publisher
American Chemical Society
Year
2007
Tongue
English
Weight
130 KB
Volume
11
Category
Article
ISSN
1083-6160

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A short and efficient synthesis of unnatural (R)-nicotine is described, in which the key step is an intramolecular hydroboration-cycloalkylation of an azido-olefin intermediate. The synthesis is achieved in only four steps, with an overall yield of 51% (or in six steps with an overall yield of 65%).