Asymmetric total synthesis of sperabillins B and D via lithium amide conjugate addition.

@article{Davies2004AsymmetricTS,
  title={Asymmetric total synthesis of sperabillins B and D via lithium amide conjugate addition.},
  author={Stephen G. Davies and Jane R. Haggitt and Osamu Ichihara and Richard J. Kelly and Michael A. Leech and Anne J Price Mortimer and Paul M. Roberts and Andrew D. Smith},
  journal={Organic \& biomolecular chemistry},
  year={2004},
  volume={2 18},
  pages={
          2630-49
        }
}
Diastereoselective conjugate addition of homochiral lithium (R)-N-allyl-N-alpha-methylbenzylamide to methyl (2E,5E)-hepatadienoate, followed by protecting group manipulation and subsequent iodocyclocarbamation allows a concise route to the core fragment, methyl (3R,5R,6R)-3,6-diamino-5-hydroxyheptanoate, of sperabillins B and D. Differentiation between the C-3 and C-6 primary amino groups of this core amino acid was readily achieved by treatment with acetone, giving the 5,6-isopropylidene and C… 
Polysubstituted piperidines via iodolactonization: application to the asymmetric synthesis of (+)-pseudodistomin D.
Conjugate addition of lithium (S)-N-allyl-N-(α-methyl-p-methoxybenzyl)amide to methyl (E,E)-hepta-2,5-dienoate furnished the corresponding β-amino ester. N-Protecting group manipulation, ring-closing
Asymmetric synthesis of 3,4-anti- and 3,4-syn-substituted aminopyrrolidines via lithium amide conjugate addition.
The diastereoselective conjugate addition of homochiral lithium amides to methyl 4-(N-allyl-N-benzylamino)but-2-enoate has been used as the key step in a simple and efficient protocol for the
Conjugate addition of lithium N-phenyl-N-(α-methylbenzyl)amide: application to the asymmetric synthesis of (R)-(-)-angustureine.
The conjugate addition of lithium (R)-N-phenyl-N-(α-methylbenzyl)amide to a range of α,β-unsaturated 4-methoxyphenyl esters proceeds with excellent levels of diastereoselectivity to give the
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A novel free-radical ring contraction of a cyclic carbamate.
TLDR
During a study on iodocyclocarbamation reactions of 2-styryl-4-piperidones, a novel ring contraction was observed and a three-electron-three-center mechanism is proposed.
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