- The synthesis of unnatural α-alkyl- And α-aryl-substituted serine derivatives
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The synthesis of α-aryl- and α-alkyl-substituted serine derivatives via [3,3]-sigmatropic rearrangement of allyl carbamates as a key step is reported. Allyl carbamates were obtained from the corresponding allyl alcohols. The former were prepared through three approaches. Aryl-substituted ones were synthesized via the Stille coupling reaction of aryl iodides with enantiomerically enriched vinyl stannanes. Conversely, alkyl-substituted allyl alcohols were prepared by an analogous strategy involving the Negishi coupling reaction of enantiomerically enriched vinyl iodides or by enzymatic kineric resolution of the corresponding racemic alcohols.
- Narczyk, Aleksandra,Stecko, Sebastian
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p. 1204 - 1213
(2020/02/22)
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- Palladium-catalyzed asymmetric quaternary stereocenter formation
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An efficient palladium catalyst is presented for the formation of benzylic quaternary stereocenters by conjugate addition of arylboronic acids to a variety of β,β-disubstituted carbocyclic, heterocyclic, and acyclic enones. The catalyst is readily prepared from PdCl2, PhBOX, and AgSbF 6, and provides products in up to 99 % enantiomeric excess, with good yields. Based on this strategy, (-)-α-cuparenone has been prepared in only two steps. Copyright
- Gottumukkala, Aditya L.,Matcha, Kiran,Lutz, Martin,De Vries, Johannes G.,Minnaard, Adriaan J.
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p. 6907 - 6914
(2012/07/01)
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