883746-36-9

Upstream product

• 1010104-72-9 2,2-Dioxo-3a,6,7,7a-tetrahydro-2λ⁶-benzo[1,2,3]oxathiazole-3-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 1863-63-4 ammonium benzoate 
• 883746-44-9 (-)-mentholsulfamoyl chloride 
• 883746-25-6 N,N-diethyl-N-{[({[(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl]-oxy}carbonyl)amino]sulfonyl}ethanaminium inner salt 
• 6705-51-7 3,4-epoxycyclohexene 
• 1010104-72-9 2,2-dioxo-3a,6,7,7a-tetrahydro-2λ⁶-1,2,3-benzoxathiazole-3-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl ester 
• 1106677-02-4 5-methyl-2-(1-methylethyl)cyclohexyl (3aR,7aS)-rel-3a,6,7,7a-tetrahydro-2λ6-1,2,3-benzothiazole-3-carboxylate 2,2-dioxide 

Downstream Products

• 1010104-73-0 (1S,6R)-(6-hydroxycyclohex-2-enyl)-carbamic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 

Relevant academic research and scientific papers

New options for the reactivity of the burgess reagent with epoxides in both racemic and chiral auxiliary modes - Structural and mechanistic revisions, computational studies, and application to synthesis

The reaction of the chiral auxiliary version of the Burgess reagent with epoxides yields diastereomeric pairs of sulfamldates, which, lead, to cis and trans amino alcohols in each, enantiomeric series. Experimental and spectral, details are provided for a

Formal total synthesis of (-)- and (+)-balanol: two complementary enantiodivergent routes from vinyloxiranes and vinylaziridines

Formal total syntheses of both enantiomers of balanol have been achieved by the preparation of the protected hexahydroazepine core 2. Two complementary routes have been investigated. The first relied on the regioselective opening of 1,2-epoxycyclohex-3-ene with a chiral-auxiliary version of the Burgess reagent to provide a diastereomeric pair of cis-fused cyclic sulfamidates. The sulfamidates were transformed to trans-amino benzoates with ammonium benzoate and, after separation, converted to (-)-2 and (+)-2 by oxidative cleavage and reductive amination. The second approach utilized vinylaziridines derived from 1-bromo-2,3-dihydroxycyclohexa-4,6-diene obtained by the whole-cell fermentation of bromobenzene with Escherichia coli JM109(pDTG601). Stereoselective opening of the aziridines generated the requisite trans-amino alcohol derivatives, which after saturation of the vinyl bromide moieties were converted to (-)-2 and (+)-2 by oxidative cleavage of the cis-diol and reductive amination. Experimental and spectral data are provided for all new compounds.

Chiral version of the burgess reagent and its reactions with oxiranes: Application to the formal enantiodivergent synthesis of balanol

An efficient formal synthesis of a (-)-balanol intermediate (25a) from cyclohexadiene oxide was accomplished in eight steps. An asymmetric version of the Burgess reagent allows for an enantiodivergent approach to both enantiomers of balanol from a racemic starting material.

Chemoenzymatic formal synthesis of (-)-balanol. Provision of optical data for an often-reported intermediate

Formal total synthesis of (-)-balanol was accomplished from bromobenzene in 13 steps via the bis-benzyl derivative 3, whose optical rotation data have been provided.

Chiral version of the Burgess reagent and its reactions with epoxides

A chiral auxiliary version of the Burgess reagent was prepared, and its reactions with epoxides were studied. Diastereomeric sulfamidates were converted to both enantiomers of protected trans-amino alcohols with ee of 84-98%. Georg Thieme Verlag Stuttgart