Development of a [3+3] cycloaddition strategy toward functionalized piperidines

Journal of Organic Chemistry

Volumn 68, Issue 11, 2003, Pages 4286-4292

  Hedley, Simon J ^a   Moran, Wesley J ^a   Price, David A ^b   Harrity, Joseph P A ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; METHANE; SUBSTITUTION REACTIONS;

CYCLOADDITION REACTIONS;

ADDITION REACTIONS;

AZIRIDINE DERIVATIVE; CYCLOPROPANE DERIVATIVE; PALLADIUM COMPLEX; PIPERIDINE DERIVATIVE; SULFONE DERIVATIVE; TOLUENE DERIVATIVE;

ARTICLE; CYCLOADDITION; ENANTIOSELECTIVITY; REACTION ANALYSIS; RING OPENING; SYNTHESIS;

AZIRIDINES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; PALLADIUM; PIPERIDINES;

EID: 0038441546     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030002c     Document Type: Article

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37. Only the major diastereomer is shown in each case in Scheme 7. The stereochemical assignment of cis- and trans-46 was not carried out due to the poor levels of selectivity observed in this case. The major epoxide diastereomer 43a was assigned based on the characteristic long-range coupling observed with one of the epoxide CH2 protons and a ring methylene proton (J = 1.5 Hz): Vedejs, E.; Dent, W. H., III; Kendall, J. T.; Oliver, P. A. J. Am. Chem. Soc. 1996, 118, 3556. Assignment of 44 is based on 2D ROESY, which is provided in the Supporting Information. Assignment of the major diastereomer of 45 is based on the coupling constants of the protons at C-5 and C-6, see Supporting Information for more details.