Expanding the medicinal chemistry toolbox: stereospecific generation of methyl group-containing propylene linkers
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Acknowledgements
We are grateful to Jotham W. Coe and Professor Steven V. Ley for stimulating discussions.
References and notes (12)
- et al.
Tetrahedron
(2001)Org. React.
(1983)Org. Prep. Proced. Int.
(1996)et al.J. Org. Chem.
(1997) - et al.
Tetrahedron: Asymmetry
(2004)et al.Organometallics
(1989) - et al.
Eur. J. Org. Chem.
(1998)et al.Liebigs Annalen/Recueil
(1997) - Ibuki, T.; Sugihara, T.; Kawakubo, H.; Sone, T. U.S. 4,533,731;...
- et al.
Helv. Chim. Acta
(1984)
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