Electrophilic amination of racemic and non-racemic allenyltitaniums. One-pot synthesis of α-hydrazinoalkynes from propargylic alcohol derivatives

Tetrahedron Letters

Volumn 40, Issue 19, 1999, Pages 3737-3740

  An, Duk Keun ^a   Hirakawa, Koichiro ^a   Okamoto, Sentaro ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

hydrazinoalkynes; Asymmetric synthesis; Electrophilic amination; Titanium and compounds

Indexed keywords

ALCOHOL DERIVATIVE; ALKYNE DERIVATIVE; CARBONIC ACID; PHOSPHATE; TITANIUM DERIVATIVE;

AMINATION; ARTICLE; CHIRALITY; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0033532193     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00584-5     Document Type: Article

References (18)

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12. [10] Synthesis of optically active α-hydrazino carbonyl compounds through electrophilic amination of chiral enolates with DAAD has been reported, see references 8a and 8b.
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16. [12] It should be noted that the stereochemical outcome of the reaction of the allenyltitanium with DAAD is different from that of the reaction with aldehydes [2]; the mechanistic rationale of the reaction is now in progress in our laboratory.
17. 1H NMR of 7 with the reported one [14]. (formula presented) The ee value of 6 was determined by GLC analysis (Chirasil-DEX CB, Chrompack) after derivatization to 9 according to the procedure shown below, while the absolute configuration was established by comparison of 9 with its antipode, 10, derived from L-leucine. (formula presented)
18. [14] Gennari C, Colombo L, Bertolini G. J. Am. Chem. Soc. 1986;108:6394-6395.