Chloride as nucleophile

Cyclopentadienylmethyl-3-methyl thietane has been obtained by substitution of a mesyloxy group using cyclo-pentadienylmagnesium chloride as nucleophile (Equation 16) <1998JOM433>. 

The same reaction works well with chloride as nucleophile to give 14 and, after reduction of the acid group and cyclisation of the alcohol 15, the epoxide 16. Such epoxides, made from many of the amino acids, now count as members of the new chiral pool. The diazonium salt 11 and the chloroacid 14 are susceptible to racemisation by enolisation and it is only after two distillations that the epoxide 16 has 97% ee. There are very detailed Organic Syntheses procedures for both these steps.6... 

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