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S) and (R) 2 hydroxymethyl pyrrolidine(2) were prepared from L proline and D glutamic acid, respectively. After acylation with propionic anhydride they gave 2 hydro xymethyl 1 propionyl pyrrolidine(3). A chiral center was introduced into (3) on alkylation with propyl bromide in the presence of lithium diisopropylamide(LDA) and (4) was formed. The alarm pheromone of leaf cutting ant, (S) and (R) 4 methyl 3 heptanone(1) were obtained from (4) by acid hydrolysis and reacting with ethyllithium. Both isomers of (1) have optical yield of 85%e.e..
(2) were prepared from L proline and D glutamic acid, respectively. After acylation with propionic anhydride they gave 2 hydro xymethyl 1 propionyl pyrrolidine (3). A chiral center was introduced into (3) (5) by alkylation with propyl bromide in the presence of lithium diisopropylamide (LDA) and (4) was formed. The alarm pheromone of leaf cutting ant, (S) and acid hydrolysis and reacting with ethyllithium. Both isomers of (1) have optical yield of 85% ee.