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Synthesis of functionalised bicyclo[4.4.0] and spiro [5.4] compounds by tin-mediated radical cyclization

✍ Scribed by Ponnusamy Shanmugam; Rajagopal Srinivasan; Krishnamoorthy Rajagopalan

Book ID
104207987
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
402 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis

Functionalised bicyclo[4.4.0] system 5, and spiro [5.4] system 10 were synthesised from the bispropargyl compound 3 and the monopropargyl compound 6 by tin-mediated radical cyclization.

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The reaction of 2,7-and 2,8-enynyl-1-ol derivatives where the ene moiety is a part of a ring with a Ti(O-i-Pr) 4 /2 i-PrMgCl reagent proceeds smoothly with excellent stereoselectivity to afford carbo-or aza-bicyclo[4.3.0] and [4.4.0] compounds, respectively, in high yields.

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