Cu(I)-catalyzed reductive aldol cyclizations: Diastereo- and enantioselective synthesis of β-hydroxylactones

Organic Letters

Volumn 7, Issue 19, 2005, Pages 4225-4228

  Lam, Hon Wai ^a   Joensuu, Pekka M ^a  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; LACTONE; LIGAND; PHOSPHINE; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; HYDROXYLATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; COPPER; CYCLIZATION; HYDROXYLATION; LACTONES; LIGANDS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PHOSPHINES; STEREOISOMERISM;

EID: 25444446131     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051649h     Document Type: Article

References (42)

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30. 2.
31. The inexpensive siloxanes polymethylhydrosiloxane (PMHS) and 1,1,3,3-tetramethylhydrosiloxane (TMDS) were evaluated.
32. The following bisphosphine ligands were studied: 1,2- bis(diphenylphosphino)ethane (DPPE), 1,2-bis(diphenyl-phosphino)butane (DPPB), 1,1′-bis(diphenylphosphino)ferrocene (DPPF), racemic 2,2′- bis(diphenylphosphino)-1,1′-binaphthyl (rac-BINAP), and (+)-1,2-bis((2S,5S)-2,5-diethylphospholano)benzene ((S,S)-Et-DuPhos).
33. 2O has shown to be a particularly convenient copper source for copper hydride generation. See refs 6b and 6e.
34. 2, and MeCN proved to be inferior solvents, although DME was similar to THF.
35. Baldwin, J. E.; Lusch, M. J. Tetrahedron 1982, 38, 2939-2947. A possible explanation for the ready cyclization of substrates 3j-m is that the copper enolate intermediate (depicted as an oxa-π-allylcopper species in Scheme 1) has significant C-bound character, which reduces its planarity and better enables ring closure.
36. The relative configurations of lactones 4b, 4e, and 4f were confirmed by X-ray crystallography, and the relative configurations of 2, 4j and 4l were confirmed by NOESY experiments. The stereochemistries of the remaining products were assigned by analogy. See Supporting Information for details.
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41. See Supporting Information for details.
42. 2O (blue) and DPPF (yellow) in THF being quickly converted into a yellow solution upon addition of TMDS, which is indicative of the reduction of copper(II) and the disappearance of the associated blue color.