Trifunctional Reagents in Organic Synthesis: Sequential, Chemoselective Reactions Leading to the Preparation of Structurally Novel Tricycles

Synlett

Volumn 1996, Issue 11, 1996, Pages 1087-1090

  Piers, Edward ^a   McEachern, Ernest J ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0006957032     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5689     Document Type: Article

References (10)

1. Piers, E.; Skerlj, R. T. Can. J. Chem. 1994, 72, 2468.
2. This chemoselective, acid-mediated protodestannylation of alkyl 2,3-bis(trimethylstannyl)alk-2-enoates is a new reaction that appears to be general. Details of a study of this process will be reported elsewhere.
3. All new compounds reported herein exhibit spectra in accord with assigned structures and gave satisfactory elemental (C, H) analyses and/or molecular mass determinations (high resolution mass spectrometry).
4. Bronk, B. S.; Lippard, S. J.; Danheiser, R. L. Organometallics 1993, 12, 3340.
5. Piers, E.; Wong, T.; Ellis, K. A. Can. J. Chem. 1992, 70, 2058.
6. Piers, E.; Friesen, R. W.; Rettig, S. J. Can. J. Chem. 1992, 70, 1385.
7. Piers, E.; McEachern, E. J.; Burns, P. A. J. Org. Chem. 1995, 60, 2322.
8. Irradiation at δ 3.38 (broad triplet, H-11) caused enhancement of the broad multiplet at δ 2.50 - 2.64 (signals due to H-1 and H-7). The resonance assignments were made by use of COSY and HMQC experiments.
9. 3Sn)
10. 1H NMR NOED experiments were carried out to establish the relative configurations of products 38 and 39.