Catalytic, Asymmetric Preparation of Ketene Dimers from Acid Chlorides

Organic Letters

Volumn 5, Issue 24, 2003, Pages 4745-4748

  Calter, Michael A ^a   Orr, Robert K ^a   Song, Wei ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; AMINE; AMMONIUM DERIVATIVE; CHLORIDE; ETHYLAMINE; KETENE DERIVATIVE;

ARTICLE; CATALYSIS; DIMERIZATION; ENANTIOSELECTIVITY; KINETICS; PROTON TRANSPORT; STEREOCHEMISTRY; SYNTHESIS;

ACIDS; CATALYSIS; CHLORIDES; DIMERIZATION; ETHYLENES; KETONES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 0348041982     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0359517     Document Type: Article

References (12)

1. For a recent review of asymmetric reactions involving ketenes, see: Orr, R. K.; Calter, M. A. Tetrahedron 2003, 59, 3545-3565.
2. (a) Nelson, S. G.; Peelen, T. J.; Wan, Z. J. Am. Chem. Soc. 1999, 121, 9742-9743.
3. (b) Yoon, T. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 2911-2912.
4. (c) Tennyson, R. L.; Romo, D. J. Org. Chem. 2000, 65, 7248-7252.
5. (d) Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Drury, W. J., III; Lectka, T. J. Am. Chem. Soc. 2000, 122, 7831-7832.
6. Calter, M. A.; Liao, W. J. Am. Chem. Soc. 2002, 124, 13127-13129 and references therein.
7. Sauer, J. C. J. Am. Chem. Soc. 1947, 69, 2444-2448.
8. Previous experiments demonstrated that the conversion of 1 into 2 proceeds in high yield and without epimerization. See: Calter, M. A.; Guo, X. J. Org. Chem. 1998, 63, 5308-5309.
9. Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Ferraris, D.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 6626-6635.
10. The kinetics experiments were conducted using TBSQN as catalyst, as this compound demonstrated optimal stability under the reaction conditions.
11. Pracejus, H. Mätje, H. J. Prakt. Chem. 1964, 24, 195-205.
12. Samtleben, R.; Pracejus, H. J. Prakt. Chem. 1972, 314, 157-169.