A novel asymmetric synthesis of 2-azetidinones from achiral precursors

Tetrahedron Letters

Volumn 40, Issue 4, 1999, Pages 585-588

  Zhou, Feng ^a,b   Detty, Michael R ^a,b   Lachicotte, Rene J ^a,b  

^a UNIVERSITY AT BUFFALO   (United States)

^b UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 PHENYLSULFONYL 4 PHENYLAZETIDIN 2 ONE; AMINE; AZETIDINONE DERIVATIVE; COPPER COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; REACTION ANALYSIS; STOICHIOMETRY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0033593425     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02473-3     Document Type: Article

References (19)

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13. 4S: 286.0300).
14. 1H NMR integrals of the methoxy singlets following the addition of chiral shift reagent {europium tris[3-(heptafluoropropylhydroxymethlene)-(+)-camphorate]}.
15. Compound 9 was not formed from either a mixture of 5 and 3 in the absence of p-methoxybenzylamine or from the carboxylic acid of 5 in the presence or absence of p-methoxybenzylamine. A plausible source of 9 is exchange of a salicylaldehyde equivalent from 3 with a benzaldehyde equivalent from acid chloride 5 (perhaps involving imine derivatives of p-methoxybenzylamine) and cylization to the coumarin.
16. The ee's of 7 were determined by chiral HPLC.
17. 1 = 3.41% and w R2 = 8.41%. The authors have deposited the atomic coordinates for the crystal structure of (3S,4S)-7 with the Cambodge Crystallographic Data Center, 12 Union Road, Cambridge, CB2 1EZ, U. K.
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