Diastereoselective addition of organozinc reagents to chiral α-imino esters

Tetrahedron Asymmetry

Volumn 13, Issue 20, 2002, Pages 2205-2209

  Chiev, Kan Pa ^a   Roland, Sylvain ^a   Mangeney, Pierre ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; ETHER DERIVATIVE; IMINO ACID; PHENYLGLYCINOL METHYL ETHER; REAGENT; SOLVENT; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ADDITION REACTION; ARTICLE; CHIRALITY; DIASTEREOISOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; TEMPERATURE;

EID: 0037131656     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00587-6     Document Type: Article

References (23)

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2. For reviews on the addition of organometallics to CN double bonds, see: (a) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895-1946; (b) Bloch, R. Chem. Rev. 1998, 98, 1407-1438.
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16. 4. Stirring for 1 h, filtration and concentration afforded the crude imino ester quantitatively, which was used without further purification. Compounds 1b-d were obtained by the same procedure.
17. Kagan and Fiaud in 1971 (see Ref. 2b) reported a complete regioselectivity in this reaction.
18. 2=(-)-8-phenylmenthyl (see Ref. 3b ).
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21. 3, filtered and concentrated at 20°C to give the aminoether in 85% yield. This procedure is applicable to hindered aminoalcohols such as norephedrine.
22. We supposed that in this case, the syn/anti selectivity was very low. This implied that the stereoselectivity must be 9:1 at the α-carbon.
23. 3).