Nonenzymatic Enantioselective Monoacetylation of Prochiral 2-Protectedamino-2-alkyl-1,3-propanediols Utilizing a Chiral Sulfonamide−Zn Complex Catalyst

Nonenzymatic Enantioselective Monoacetylation of Prochiral 2-Protectedamino-2-alkyl-1,3-propanediols Utilizing a Chiral Sulfonamide−Zn Complex Catalyst

Treatment of a chiral sulfonamide with Et2Zn gave quantitatively its Zn complex and then the structure was determined by X-ray crystallographic analysis. Reaction of prochiral N-Boc-2-amino-2-alkyl-1,3-propanediols with Ac2O in the presence of 5 mol % of chiral sulfonamide−Zn complex catalyst afford...

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Veröffentlicht in:Organic letters 2007-02, Vol.9 (3), p.509-512
Hauptverfasser: Honjo, Takashi, Nakao, Michiyasu, Sano, Shigeki, Shiro, Motoo, Yamaguchi, Kentaro, Sei, Yoshihisa, Nagao, Yoshimitsu
Format: Artikel
Sprache:eng
Schlagworte:
Acetylation
Alkylation
Amines - chemistry
Catalysis
Models, Chemical
Models, Molecular
Organometallic Compounds - chemistry
Propylene Glycols - chemical synthesis
Stereoisomerism
Sulfonamides - chemistry
Zinc - chemistry
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Zusammenfassung:Treatment of a chiral sulfonamide with Et2Zn gave quantitatively its Zn complex and then the structure was determined by X-ray crystallographic analysis. Reaction of prochiral N-Boc-2-amino-2-alkyl-1,3-propanediols with Ac2O in the presence of 5 mol % of chiral sulfonamide−Zn complex catalyst afforded the corresponding chiral monoacetyl products in 70−92% yields with 70−88% ee values. The proposed mechanism for the catalytic monoacetylation of a prochiral 1,3-propanediol was presented on the basis of CSI-MS analysis.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol063063g