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Volumn 47, Issue 33, 2008, Pages 6244-6246

Entry to heterocycles based on indium-catalyzed Conia-ene reactions: Asymmetric synthesis of (-)-salinosporamide A

Author keywords

Conia ene reaction; Cyclization; Heterocycles; Indium; Synthetic methods

Indexed keywords

CONIA-ENE REACTION; CYCLIZATION; HETEROCYCLES; INDIUM; SYNTHETIC METHODS;

EID: 51649114068     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200801967     Document Type: Article
Times cited : (130)

References (39)
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    • and references therein. For an intermolecular version of the Conia-ene reaction, see
    • For an intermolecular version of the Conia-ene reaction, see: K. Endo, T. Hatakeyama, M. Nakamura, E. Nakamura, J. Am. Chem. Soc. 2007, 129, 5264-5271, and references therein.
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    • For related metal-catalyzed cyclization reactions that produce 3-methylene pyrrolidines and tetrahydrofurans, see: a
    • For related metal-catalyzed cyclization reactions that produce 3-methylene pyrrolidines and tetrahydrofurans, see: a) X. Marat, N. Monteiro, G. Balme, Synlett 1997, 845-847;
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    • For related metal-catalyzed cyclization reactions that produce lactams, see: a
    • For related metal-catalyzed cyclization reactions that produce lactams, see: a) E. C. Minnihan, S. L. Colletti, F. D. Toste, H. C. Shen, J. Org. Chem. 2007, 72, 6287-6289;
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    • Isolation: R. H. Feling, G. O. Buchanan, T. J. Mincer, C. A. Kauffman, P. R. Jensen, W. Fenical, Angew. Chem. 2003, 115, 369-371;
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    • Total synthesis: a) E. J. Corey, P. Saravanan, L. R. Reddy, J. Am. Chem. Soc. 2004, 126, 6230-6231;
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    • Racemic synthesis: a) N. P. Mulholland, G. Pattenden, I. A. S. Walters, Org. Biomol. Chem. 2006, 4, 2845-2846;
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    • This follows the reaction mechanism for the related intermolecular In(OTf)3-catalyzed reaction proposed by Nakamura et al, see Ref, 6
    • 3-catalyzed reaction proposed by Nakamura et al., see Ref. [6].
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    • and references therein
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    • The enantiomeric purities for each epimer of this mixture were determined by HPLC on a chiral stationary phase and were both 93% ee
    • The enantiomeric purities for each epimer of this mixture were determined by HPLC on a chiral stationary phase and were both 93% ee.
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    • The enantiomeric purity (90% ee) of 12 suggested production by a silica gel promoted Conia-ene reaction rather than cyclization through the corresponding achiral allenylamide.
    • The enantiomeric purity (90% ee) of 12 suggested production by a silica gel promoted Conia-ene reaction rather than cyclization through the corresponding achiral allenylamide.


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