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Volumn , Issue 2, 1997, Pages 176-182

Stereoselective synthesis of enantiopure β-amino alcohols via nucleophilic β-amino-α-hydroxyalkylation by means of 1-lithiated 2-[N-(diphenylmethyleneamino)]alkyl carbamates

Author keywords

1 lithioalkyl carbamates; deprotonation; imines; amino alkanols

Indexed keywords

AMINOALCOHOL;

EID: 0031057958     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1155     Document Type: Article
Times cited : (10)

References (25)
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    • The deuteriated compounds 10a and 101, in a stricter sense, do not match with the Masamune convention. Masamune, S.; Ali, S.A.; Snitman, D.L.; Garvey, D.S. Angew. Chem. 1980, 92, 573; Angew. Chem. Int. Ed. Eng. 1980, 19, 557.
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    • The deuteriated compounds 10a and 101, in a stricter sense, do not match with the Masamune convention. Masamune, S.; Ali, S.A.; Snitman, D.L.; Garvey, D.S. Angew. Chem. 1980, 92, 573; Angew. Chem. Int. Ed. Eng. 1980, 19, 557.
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    • note
    • The prefix ent means that the addressed compound is the mirror image of its enantiomer shown in the formula scheme.
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    • For the problems arising from double stereoselection in (-)-sparteine-mediated deprotonations, see also: Haller, J.; Hense, T.; Hoppe, D. Liebigs Ann. Chem. 1996, 489.
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    • note
    • The deprotonation reaction with sec-butyllithium/TMEDA (MeOD as electrophile) yielded only 5% of an EjZ mixture of the sec-butyl-substituted adduct and 15% of the 1-deuteriated carbamate (> 95% D). The reaction with sec-butyllithium/(-)-sparteine was even more complicated and gave 35% of the sec-butyl-substituted adduct and in addition a mixture of the 3-, the 1-deuteriated carbamate and 14 (18%, 9:29:62).


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