Enantioselective synthesis of alpha-ionone derivatives using an anti S(N)2' substitution of functionalized zinc organometallics |
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Authors: | Soorukram Darunee Knochel Paul |
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Institution: | Department Chemie, Ludwig-Maximilians-Universit?t, Butenandtstrasse 5-13, 81377, München, Germany. |
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Abstract: | reaction: see text] The allylic substitution of sterically hindered (2-iodocycloalkyl)phosphates proceeds with complete anti S(N)2' stereoselectivity with mixed diorganozincs of the type RZnCH(2)SiMe(3) in the presence of CuCN.2LiCl. Only the group R of the copper-zinc reagent is transferred in the allylic substitution. This method was used to prepare odoriferous substances such as (R)-alpha-ionone in 97% ee and (R)-dihydro-alpha-ionone in 98% ee. |
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