Origin of π-facial stereoselectivity in nucleophilic additions. Application of the exterior frontier orbital extension model to imines and iminium ions

Journal of Organic Chemistry

Volumn 64, Issue 15, 1999, Pages 5396-5400

  Tomoda, Shuji ^a   Senju, Takatoshi ^a   Kawamura, Mitsuhiro ^b   Ikeda, Takafumi ^b  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE; IMINE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPUTER PROGRAM; MODEL; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033597872     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990018w     Document Type: Article

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23. Experimental procedures of these reactions followed those described in ref 12e. The stereochemical assignments of the products derived from the glycine imine or the piperazine imminium of tropone were made as follows. The stereochemistries of the products derived from the piperazine imminium were assigned by the NOESY method and the exo/endo ratio was determined by integration of the N-methyl protons (δ = 2.28 for the exo isomer and 2.20 for the endo isomer) as well as the bridge head protons (δ = 3.19 for the exo isomer and 3.08 for the endo isomer). The stereochemical assignment of the amine from the glycine inline, obtained as a single isomer, was made by conversion into the corresponding endo-piperazine derivative.
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