176199-53-4

Upstream product

• 930-30-3 cyclopent-2-enone 
• 878480-86-5 (1R,3R,4S)-2-ethylcarboxymethyl-3-[(1R,4S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]-2-thioniabicyclo[2.2.1]heptane tetrafluoroborate 

Downstream Products

• 188885-85-0 (1S,5R,6S)-2-oxo-bicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Asymmetric sulfonium ylide mediated cyclopropanation: Stereocontrolled synthesis of (+)-LY354740

The reaction of ester-stabilized sulfonium ylides with cyclopentenone to give (+)-5 ((1S,5R,6S)-ethyl 2-oxobicyclo[3.1.0]hexane-6-carboxylate), an important precursor to the pharmacologically important compound (+)-LY354740, has been studied using chiral sulfides operating in both catalytic (sulfide, Cu(acac)2, ethyl diazoacetate. 60°C) and stoichiometric modes (sulfonium salt, base, room temperature). It was found that the reaction conditions employed had a major influence over both diastereo- and enantio-selectivity. Under catalytic conditions, good enantioselectivity with low diastereoselectivity was observed, but under stoichiometric conditions low enantioselectivity with high diastereoselectivity was observed. When the stoichiometric reactions were conducted at high dilution, diastereoselectivity was reduced. This indicated that base-mediated betaine equilibration was occurring (which is slow relative to ring closure at high dilution). Based on this model, conditions for achieving high enantioselectivity were established as follows: use of a preformed ylide, absence of base, hindered ester (to reduce ylide-mediated betaine equilibration), and low concentration. Under these conditions high enantioselectivity (95% ee) was achieved, albeit with low diastereocontrol. Our model for selectivity has been applied to other sulfonium ylide mediated cyclopropanation reactions and successfully accounts for the diastereoselectivity observed in all such reported reactions to date.

Excitatory amino acid receptor modulators

Compounds of the formula (I) in which: R1 is (CH2)nY; n is 1 or 2; Y is NHSO2R2 or X1—W—X2—R3; X1 is O or NH; W is C═O, C═S, C═NH, or SO2; X2 is O or NH, provided that X1 and X2 are not both O; R2 is C1-10 alkyl; C2-10 alkenyl; C2-10 alkynyl; aryl; aryl-C1-10 alkyl; aryl-C2-10 alkenyl; aryl-C2-10alkynyl; C3-8 cycloalkyl or C3-8-cycloalkyl-C1-10 alkyl; and R3 is hydrogen, C1-10alkyl; C2-10 alkenyl; C2-10 alkynyl; aryl; aryl-C1-10 alkyl; aryl-C2-10 alkenyl; aryl-C2-10 alkynyl; C3-8 cycloalkyl; or C3-8-cycloalkyl-C1-10 alkyl; or a salt or ester thereof, modulate metabotropic glutamate receptor function and are useful in treating disorders of the central nervous system.

Excitatory amino acid receptor modulators

Compounds of formula (I) in which R1is halo-C1-10alkyl; halo-C2-10alkenyl; or (CH2)nY in which n is 1 or 2 and Y is OH, CN, N3, OR3, SH, S(O)pR4, S(O)3H, NH2, NHR5, NR6R7, NHCOR8, NO2, CO2H, CONHR9, 1H-tetrazol-5-yl, 5-phenyltetrazol-2-yl or PO3H2; R3, R5, R6, R7, R8and R9are each selected independently from C1-4alkyl, aryl and aryl-C1-4alkyl; R4is selected from C1-4alkyl, aryl, aryl-C1-4alkyl, and 1H-tetrazol-5-yl, carboxy-(1-4C)alkyl and 1H-tetrazol-5-yl-C1-4alkyl; and p is 0, 1, 2 or 3; or a salt or ester thereof, provided that R1is not methoxymethyl, modulate metabotropic glutamate receptor function and are useful in treating disorders of the central nervous system.