Diastereoselective peracid epoxidation: Control of the face selectivity via functional group tuning and proper choice of epoxidation reagent

Tetrahedron Letters

Volumn 39, Issue 20, 1998, Pages 3213-3214

  Jensen, Annika Jenmalm ^a   Luthman, Kristina ^a,b  

^a UPPSALA UNIVERSITY   (Sweden)

^b UNIVERSITY OF TROMSØ   (Norway)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIC ACID DERIVATIVE; CARBAMIC ACID DERIVATIVE; PERACETIC ACID;

ARTICLE; EPOXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032516318     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00393-1     Document Type: Article

References (8)

1. 2O to urea-hydrogen peroxide (UHP). See; Cooper, M. S.; Heaney, H.; Newbold, A.J.; Sanderson, W. R. Synlett 1990, 533-535
2. 2. a) Jenmalm, A.; Berts, W.; Li, Y.-L.; Luthman, K.; Csöregh, I.; Hacksell, U. J. Org. Chem. 1994, 59, 1139-1148;
3. b) Jenmalm, A.; Berts, W.; Luthman, K.; Csöregh, I.; Hacksell, U. J. Org. Chem. 1995, 60, 1026-1032 and reference 1 therein;
4. c) Kocovsky, P.; Stary, I. J. Org. Chem. 1990, 55, 3236-3243.
5. 3. All compounds reported herein gave spectral data consistent with the assigned structures as well as satisfactory elemental analyses.
6. 4. Directing effects using different peracids: McKittrick, B. A.; Ganem, B. Tetrahedron Lett. 1985, 26, 4895-4898.
7. 5. Low reactivity of disubstituted carbamates: Rotella, D. P. Tetrahedron Lett, 1989, 30, 1913-1916; see also ref. 2c.
8. 6. Shambayati, S.; Blake, J. F.; Wierschke, S. G.; Jorgensen, W. L.; Schreiber, S.S. J. Am. Chem. Soc. 1990, 112, 697-703.