L-valinol and L-phenylalaninol-derived 2-imidazolidinones as chiral auxiliaries in asymmetric aldol reactions

Tetrahedron Letters

Volumn 41, Issue 10, 2000, Pages 1505-1508

  Hyeon Kim, Taek ^a   Lee, Gue Jae ^a  

^a Chonnam National University   (South Korea)

Author keywords

Asymmetric aldol reaction; Chiral N propionyl 2 imidazolidinones; L valinol; L phenylalaninol

Indexed keywords

2 IMIDAZOLIDINONE DERIVATIVE; ALDEHYDE DERIVATIVE; AMINO ACID DERIVATIVE; BORON DERIVATIVE; PHENYLALANINE DERIVATIVE; VALINE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0343415548     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02325-4     Document Type: Article

References (26)

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15. To lower the reactivity of the carbonyl group in 2-oxazolidinone, 2-imidazolidinone 2 was used in the asymmetric synthesis of difluorocyclopropanes through the Michael addition of lithium enolate of 2; see: Taguchi, T.; Shibuya, A.; Sasaki, H.; Endo, J.-i.; Morikawa, T.; Shiro, M. Tetrahedron: Asymmetry 1994, 5, 1423-1426.
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20. 3) 174.8, 152.8, 139.0, 136.4, 129.7, 129.2, 129.0, 127.3, 124.7, 119.5, 51.9, 46.7, 38.9, 29.8, 9.0.
21. 3) 178.7, 151.9, 138.4, 135.8, 129.4, 129.0, 128.8, 127.2, 124.7, 119.6, 76.8, 51.5, 46.4, 39.5, 38.5, 30.6, 19.5, 18.9, 10.2
22. syn (2-4 Hz); see: (a) Kleschick, W. A.; Buse, C. T.; Heathcock, C. H. J. Am. Chem. Soc. 1977, 99, 247-248.
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25. Prasad and co-workers reported that compound 6 was also prepared from the ring opening of chiral 1,2-aminoalcohol-derived oxazoline with aniline followed by cyclization of the resulting N-acylated 1,2-diamine with phosgene. This method, however, has some limitations in the diversity of 6; see: Konigsberger, K.; Prasad, K.; Repic, O.; Blacklock, T. J. Tetrahedron: Asymmetry 1997, 8, 2347-2354.
26. For the use of 2 as a chiral auxiliary so far; see Refs. 6 and 14.