The highly trans-selective Darzens reaction via ammonium ylides

Synlett

Volumn , Issue 5, 2005, Pages 842-844

  Kimachi, Tetsutaro ^a   Kinoshita, Hiroyo ^a   Kusaka, Kumiko ^a   Takeuchi, Yukiko ^a   Aoe, Mai ^a   Ju Ichi, Motoharu ^a  

^a MUKOGAWA WOMEN'S UNIVERSITY   (Japan)

Author keywords

2,3 diaryl epoxides; Ammonium ylides; Darzens reaction

Indexed keywords

1,4 DIAZABICYCLO[2.2.2]OCTANE; AMMONIUM DERIVATIVE; BENZYLTRIETHYLAMMONIUM CHLORIDE; EPOXIDE; UNCLASSIFIED DRUG;

ARTICLE; DARZENS REACTION; DIASTEREOISOMER; ELECTRON; ELECTRON TRANSPORT; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 15944424623     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-864799     Document Type: Article

References (16)

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8. Jonczyk, A.; Konarska, A. Synlett 1999, 1085.
9. 2O: C, 62.7; H, 9.65; N, 8.12. Found: C, 62.55; H, 9.99; N, 8.12.
10. Quaternary ammonium salts containing methyl groups are known to promote 2,3-Stevens-type rearrangement reaction under strong basic condition. See: Marko, I. E. In Comprehensive Organic Synthesis, Vol. 3; Trost, B., Ed.; Pergamon Press: Oxford England, 1991, 913.
11. 2.
12. Quinuclidine (the second N of DABCO is replaced by CH) was also tried as an amine candidate. The ammonium salt was formed but it was too moisture sensitive to be isolated. When one-pot and successive preparation of trans-2,3-diaryl epoxide was carried out using quinuclidine, 2h was obtained in 89%. Thus, the role of the second N of DABCO is not clear to date.
13. When carbonyl compounds such as aliphatic aldehydes and ketones, other than aryl aldehydes were used under the reaction condition, no epoxides were formed and carbonyl compounds were recovered.
14. According to the literature method,10 we have tried the reaction using benzylic chloride [e.g. (p-chloromethyl)benzonitrile, p-nitrobenzyl chloride] and benzaldehyde in the presence of phase-transfer catalyst. Corresponding epoxides were obtained in 88% and 70%, respectively, as diastereomeric mixtures.
15. (a) Dilling, W. L.; Hickner, R. A.; Farber, H. A. J. Org. Chem. 1967, 32, 3489.
16. (b) Taranko, L. B.; Perry, R. H. Jr. J. Org. Chem. 1969, 34, 226.