5-Carboxy-2-azabicyclo[2.1.1]hexanes as precursors of 5-halo, amino, phenyl, and 2-methoxycarbonylethyl methanopyrrolidines.
Novel 5-X-substituted-2-azabicyclo[2.1.1]hexanes (X = 5-syn-Cl, -Br, -I, -Ph, -NHCOOR (R = Me, Bn, t-Bu), -CH2CH2COOMe and X = 5-anti-Br, -I, -Ph) were synthesized from the X = 5-syn-carboxy derivative. New 5-anti-X-2-azabicyclo[2.1.1]hexanes, X = NHCOOR (R = Me, Bn), were prepared stereoselectively from the X = 5-anti-carboxy substrate.
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. grantkrow@aol.com
Grant R
GR
Krow
Qiuli
Q
Huang
Guoliang
G
Lin
Ryan A
RA
Centafont
Andrew M
AM
Thomas
Deepa
D
Gandla
Charles
C
Debrosse
Patrick J
PJ
Carroll
D000143:Acids / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis / Q000737:chemistry*; D004952:Esters; D006586:Hexanes / Q000138:chemical synthesis / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry; D016877:Oxidants / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000143:Acids; D019086:Bridged Bicyclo Compounds, Heterocyclic; D004952:Esters; D006586:Hexanes; D007454:Iodides; D016877:Oxidants; D011759:Pyrrolidines