Diastereoselectivity in Nucleophilic Addition Reactions to (α-βDialkoxyacyl)silanes: An Operationally Useful Route to Optically Active 1,2,3-syn -Triols

Journal of Organic Chemistry

Volumn 55, Issue 25, 1990, Pages 6071-6073

  Cirillo, Pier F ^a   Panek, James S ^a  

^a BOSTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000081048     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00312a005     Document Type: Article

References (55)

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12. Two reviews have appeared recently: (1) Ricci, A.; Degl’Innocenti, A. Synthesis 1989, 647.
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14. Recently Ohno and co-workers have demonstrated that enhanced levels of 1,2-asymmetric induction in the Cram sense can be achieved in nonchelation-controlled addition reactions on (a-alkylacyl)silanes, see: Nakada, M.; Urano, Y.; Kobayashi, S.; Ohno, M. J. Am. Chem. Soc. 1988, 110. 4826.
15. For some alternative approaches to the synthesis of 1,2,3-syn-triol units, see: (a) Bernardi, A.; Cardani, S.; Colombo, L.; Poli, G.; Schim-perna, G.; Scholastico, C. J. Org. Chem. 1987, 52, 888.
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24. For a very recent discussion, see: Chen, X.; Hortelano, E. R.; Eliel, E. L. J. Am. Chem. Soc. 1990, 112, 6130.
25. The precise reasons for the poor chelating ability of the silyl ether is a subject of debate and has been attributed to p-d back bonding of the nonbonded pairs of electrons on oxygen to silicon and to the steric bulk of the TBS silyl ether. See: (c) Keck, G. E.; Boden, E. P. Tetrahedron Lett. 1984, 25, 265.
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29. For its observation in the context of an Ireland Claisen rearrangement in the synthesis of pseudo-monic acid, see: Barrish, J. C.; Lee, H. L.; Baggiolini, E. G.; Uskokovic, M. R. J. Org. Chem. 1987, 52, 1372.
30. For leading references citing the older literature thoroughly, see: (g) Shambayati, S.; Blake, J. F.; Wierschke, S. G.; Jorgensen, W. L.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 697.
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43. The structurally related aldehyde ii was allylated under the same conditions and was found to undergo nucleophilic attack with similar levels of diastereoselectivity:
44. Aldehyde ii could be easily obtained in 75% yield by subjecting the phenyl-substituted acylsilane 3e to standard hydrogenation conditions (ethanol/Pd-C catalyst, room temperature) (Panek, J, S.; Cirillo, P. F. Tetrahedron Lett., submitted).
45. Changing the Lewis acid to TiCl4or SnCl4resulted in similar or higher levels of selectivity, but the reaction was complicated by the loss of the MOM or BOM protecting group. Interestingly, no reaction was observed with MgBr2 even at room temperature with 4 molar equiv of the Lewis acid(cf., ref 3b, 6c,d).
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48. References Id and 2.
49. The use of n-Bu4NF in THF at -10 °C over 4 days resulted in lower yields (17%).
50. The use of ZnBr2 or Znl2results in similar levels of diastereoselectivity. The reactions with these Lewis acids are extremely slow at -30 °C, being performed therefore at 0 °C in 8 h without the formation in situ of the silyl ether resulting from Brook rearrangement of the addition product.
51. For a similar desilylation of an allylic position, involving a Brook rearrangement, see: Koreeda, M.; Koo, S. Tetrahedron Lett. 1990, 31, 831 and references therein.
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