Asymmetric synthesis of polyhydroxylated pyrrolizidines via transannular iodoamination with concomitant N-debenzylation

Organic Letters

Volumn 13, Issue 7, 2011, Pages 1594-1597

  Brock, E Anne ^a   Davies, Stephen G ^a   Lee, James A ^a   Roberts, Paul M ^a   Thomson, James E ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79953165403     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol103090z     Document Type: Article

References (32)

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10. The α-methylbenzyl cation is then trapped by MeCN, with the ensuing Ritter reaction giving racemic α-methylbenzyl acetamide.
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13. For a previous synthesis of (±)-7a- epi -hyacinthacine A1, see: Affolter, O.; Baro, A.; Frey, W.; Laschat, S. Tetrahedron 2009, 65, 6626 For a previous synthesis of (+)-7a- epi -hyacinthacine A1, see: Izquierdo, I.; Plaza, M. T.; Tamayo, J. A.; Franco, F.; Sánchez-Cantalejo, F. Tetrahedron 2010, 66, 3788 For a previous synthesis of (-)-7a- epi -hyacinthacine A1, see: Garrabou, X.; Gomez, L.; Joglar, J.; Gil, S.; Parella, T.; Bujons, J.; Clapes, P. Chem.-Eur. J. 2010, 16, 10691
14. Davies, S. G.; Durbin, M. J.; Goddard, E. C.; Kelly, P. M.; Kurosawa, W.; Lee, J. A.; Nicholson, R. L.; Price, P. D.; Roberts, P. M.; Russell, A. J.; Scott, P. M.; Smith, A. D. Org. Biomol. Chem. 2009, 7, 761
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19. 3 gave (R)- N -but-3-enyl- N -(α-methylbenzyl)amine; subsequent deprotonation with n -BuLi in THF generated a yellow solution of lithium (R)- N -but-3-enyl- N -(α-methylbenzyl)amide 12.
20. For determination of the "matched" and "mismatched" reaction pairings for the additions of the antipodes of lithium N -benzyl- N -(α-methylbenzyl)amide to chiral α,β-unsaturated ester 11, see ref 10.
21. Both the α-hydroxy-β-amino ester (14 or 18) and the corresponding β-amino ester (14P or 18P) were present in the crude reaction mixture.
22. For selected examples, see: Bunnage, M. E.; Burke, A. J.; Davies, S. G.; Millican, N. L.; Nicholson, R. L.; Roberts, P. M.; Smith, A. D. Org. Biomol. Chem. 2003, 1, 3708
23. Abraham, E.; Candela-Lena, J. I.; Davies, S. G.; Georgiou, M.; Nicholson, R. L.; Roberts, P. M.; Russell, A. J.; Sánchez-Fernández, E. M.; Smith, A. D.; Thomson, J. E. Tetrahedron: Asymmetry 2007, 18, 2510
24. Abraham, E.; Davies, S. G.; Millican, N. L.; Nicholson, R. L.; Roberts, P. M.; Smith, A. D. Org. Biomol. Chem. 2008, 6, 1655
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27. Chippindale, A. M.; Davies, S. G.; Iwamoto, K.; Parkin, R. M.; Smethurst, C. A. P.; Smith, A. D.; Rodriguez-Solla, H. Tetrahedron 2003, 59, 3253
28. Maynard, H. D.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 4137
29. Crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 805283.
30. 3 gave (R)- N -but-3-enyl- N -(α-methyl- p -methoxybenzyl) amine; subsequent deprotonation with n -BuLi in THF generated a yellow solution of lithium (R)- N -but-3-enyl- N -(α-methyl- p -methoxybenzyl)amide 17.
31. See also: Srihari, P.; Bhunia, D. C.; Sreedhar, P; Yadav, J. S. Synlett 2008, 7, 1045
32. Crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 805284.