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Volumn , Issue 13, 2007, Pages 1363-1365

Reversibility in the boron-mediated ketone-ketone aldol reaction

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BORON; KETONE;

ALDOL REACTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION KINETICS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 33947535326 PISSN: 13597345 EISSN: None Source Type: Journal
DOI: 10.1039/b617094c Document Type: Article

Times cited : (12)

References (13)

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- B. M. Kim, S. F. Williams and S. Masamune, in Comprehensive Organic Synthesis, ed., B. M. Trost, and, I. Fleming,, Pergamon Press, Oxford, 1991, vol. 2, pp. 239-275
- (1991) Comprehensive Organic Synthesis, Ed.
- Kim, B.M.¹ Williams, S.F.² Masamune In, S.³

2
- 0001822874
- I. Paterson C. J. Cowden Org. React. 1997 51 1 200
- (1997) Org. React. , vol.51 , pp. 1-200
- Paterson, I.¹ Cowden, C.J.²

3
- 13444292381
- K. M. Cergol P. Turner M. J. Coster Tetrahedron Lett. 2005 46 1505 1509
- (2005) Tetrahedron Lett. , vol.46 , pp. 1505-1509
- Cergol, K.M.¹ Turner, P.² Coster, M.J.³

4
- 0001138389
- H. C. Brown R. K. Dhar G. Kumaraperumal B. Singaram J. Org. Chem. 1992 57 499 504
- (1992) J. Org. Chem. , vol.57 , pp. 499-504
- Brown, H.C.¹ Dhar, R.K.² Kumaraperumal, G.³ Singaram, B.⁴

5
- 0000791156
- H. C. Brown R. K. Dhar K. Ganesan K. B. Singaram J. Org. Chem. 1992 57 2716 2721
- (1992) J. Org. Chem. , vol.57 , pp. 2716-2721
- Brown, H.C.¹ Dhar, R.K.² Ganesan, K.³ Singaram, K.B.⁴

6
- 33947517988
- Brown and co-workers established that the boron enolate formation is irreversible and under kinetic control, ref. 3
- Brown and co-workers established that the boron enolate formation is irreversible and under kinetic control, ref. 3

7
- 33751553232
- A. Bernardi A. M. Capelli C. Gennari J. Org. Chem. 1990 55 3576 3581
- (1990) J. Org. Chem. , vol.55 , pp. 3576-3581
- Bernardi, A.¹ Capelli, A.M.² Gennari, C.³

8
- 0028137706
- A. Bernardi A. Comotti C. Gennari C. T. Hewkin J. M. Goodman A. Schlapbach I. Paterson Tetrahedron 1994 50 1227 1242
- (1994) Tetrahedron , vol.50 , pp. 1227-1242
- Bernardi, A.¹ Comotti, A.² Gennari, C.³ Hewkin, C.T.⁴ Goodman, J.M.⁵ Schlapbach, A.⁶ Paterson, I.⁷

9
- 0028853930
- Evans and co-workers showed that boron-mediated ketone-aldehyde aldol reactions are not reversible, even at high temperature, see:
- A. Bernardi C. Gennari J. M. Goodman I. Paterson Tetrahedron: Asymmetry 1995 6 2613 2636
- (1995) Tetrahedron: Asymmetry , vol.6 , pp. 2613-2636
- Bernardi, A.¹ Gennari, C.² Goodman, J.M.³ Paterson, I.⁴

10
- 33845556160
- D. A. Evans J. V. Nelson E. Vogel T. R. Taber J. Am. Chem. Soc. 1981 103 3099 3111
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- Evans, D.A.¹ Nelson, J.V.² Vogel, E.³ Taber, T.R.⁴

11
- 33947524425
- 3N·HCl, which was compacted by centrifugation
- 3N·HCl, which was compacted by centrifugation

13
- 33947504282
- The diastereoselectivities shown in Scheme 1 for formation of aldol adducts 5, 6, 8 and 9 could therefore result from differences in the stability of the diastereomeric boron aldolates
- The diastereoselectivities shown in Scheme 1 for formation of aldol adducts 5, 6, 8 and 9 could therefore result from differences in the stability of the diastereomeric boron aldolates

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