doi: 10.1021/ol049221q.
Enantioselective synthesis of alpha-ionone derivatives using an anti S(N)2' substitution of functionalized zinc organometallics
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- PMID: 15228291
- DOI: 10.1021/ol049221q
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Enantioselective synthesis of alpha-ionone derivatives using an anti S(N)2' substitution of functionalized zinc organometallics
Org Lett.
.
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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