Pentacoordinate vs. Tetracoordinate complexation for alkoxycarbonyl compounds with dialkylboron triflates and trifluoroacetates?

Tetrahedron Letters

Volumn 39, Issue 44, 1998, Pages 8105-8108

  Ooi, Takashi ^a   Uraguchi, Daisuke ^a   Maruoka, Keiji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKOXYCARBONYL; CARBONYL DERIVATIVE; ORGANOBORON DERIVATIVE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; COMPLEX FORMATION; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY;

EID: 0032578751     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01798-5     Document Type: Article

References (13)

1. (1) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc., 1998, 120, 5327. See also: Ooi, T.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc., 1997, 119, 5754.
2. (1) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc., 1998, 120, 5327. See also: Ooi, T.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc., 1997, 119, 5754.
3. (2) Negishi, E. "Organometallics in Organic Synthesis"; John Wiley & Sons, New York, 1980.
4. (3) Santelli, M.; Pons, J.-M. "Lewis Acids and Selectivity in Organic Synthesis"; CRC Press: Boca Raton, 1995.
5. 2H at 25 °C for several hours.
6. 2BOTf (R = Et, Bu) as Lewis acids: Tanigucgi, N.; Kinoshita, H.; Inomata, K.; Kotake, H. Chem. Lett. 1984, 1347. See also: Mukaiyama, T.; Inoue, T. Chem. Lett. 1976, 559
7. 2BOTf (R = Et, Bu) as Lewis acids: Tanigucgi, N.; Kinoshita, H.; Inomata, K.; Kotake, H. Chem. Lett. 1984, 1347. See also: Mukaiyama, T.; Inoue, T. Chem. Lett. 1976, 559
8. (6) Reetz, M. T. Angew. Chem. Int. Ed. Engl. 23, 556 (1984).
9. + (δ 162.23 and δ 161.94, respectively).
10. (8) Lee, D. Y., Maetin, J. C. J. Am. Chem. Soc. 106, 5745 (1984).
11. 11B NMR chemical shifts are highly dependent on the ligands and structural types of organoboron compounds, and on the coordination number of the B atom. However, as the general tendecy, the higher coordination number of the B atom in organoboron compounds causes the more upfield shift. See also ref 8.
12. 2BOTf may form a tetracoordinate structure due to self-association.
13. 3)(MeO)CC(=O)O-9-BBN gave only a trace of alcohol 3 due to their feeble Lewis acidity.