22173-21-3

Upstream product

• 636-82-8 cyclohexene-1-carboxylic acid 
• 75-65-0 tert-butyl alcohol 
• 98-89-5 Cyclohexanecarboxylic acid 
• 16537-05-6 tert-butyl cyclohexanecarboxylate 
• 60774-55-2 2-Methylthiocyclohexancarbonsaeure-tert.-butylester 

Downstream Products

• 151294-67-6 (1S,2R)-2-[Benzyl-((R)-1-phenyl-ethyl)-amino]-cyclohexanecarboxylic acid tert-butyl ester 
• 158414-47-2 (1R,2S,αS)-tert-butyl 2-(N-benzyl-N-α-methylbenzylamino)cyclohexanecarboxylate 
• 188818-73-7 t-Butyl (+/-)-cis-2-aminocyclohexanecarboxylate 
• 1027260-18-9 Carbonic acid ethyl ester (E)-3-{(1R,2R)-2-[((R)-1-phenyl-ethyl)-(3-trimethylsilanyl-prop-2-ynyl)-amino]-cyclohexyl}-allyl ester 
• 158414-45-0 (1S,2R)-2-aminocyclohexanecarboxylic acid hydrochloride 
• 158414-45-0 (1S,2S)-(+)-2-aminocyclohexane-1-carboxylic acid hydrochloride 
• 158414-45-0 (R,R)-trans-2-aminocyclohexanecarboxylic acid hydrochloride 
• 158414-45-0 (-)-(1R,2S)-2-aminocyclohexanecarboxylic acid hydrochloride 
• 151379-88-3 tert-butyl (1R,2R,αR)-2-(N-benzyl-N-α-methylbenzylamino)cyclohexane-1-carboxylate 
• 158414-49-4 tert-butyl (1S,2S,αS)-2-(N-benzyl-N-α-methylbenzylamino)cyclohexane-1-carboxylate 

Relevant academic research and scientific papers

Palladium-Catalyzed α,β-Dehydrogenation of Esters and Nitriles

A highly practical and general palladium-catalyzed methodology for the α,β-dehydrogenation of esters and nitriles is reported. Generation of a zinc enolate or (cyanoalkyl)zinc species followed by the addition of an allyl oxidant and a palladium catalyst results in synthetically useful yields of α,β-unsaturated esters, lactones, and nitriles. Preliminary mechanistic investigations are consistent with reversible β-hydride elimination and turnover-limiting, propene-forming reductive elimination.

Iridium(I)-catalyzed vinylic C-H borylation of 1-cycloalkenecarboxylates with bis(pinacolato)diboron

Ir(i)-catalyzed C-H borylation of 1-cycloalkenecarboxylic derivatives with bis(pinacolato)diboron affords various alkenylboronates with functional groups in excellent yields. This reaction was also used in a one-pot borylation/Suzuki-Miyaura cross-coupling procedure.

Conjugate allylation of cyclic α,β-unsaturated esters

The conjugate allylation of a homologous series of α,β- unsaturated cyclic esters 8-10 by addition of diallylcuprate (method A), fluoride ion catalyzed addition of trimethylallylsilane (method B), and aluminium tris(2,6-diphenylphenoxide) (ATPH)-mediated addition of allyllithium (method C) was investigated. Method A was not selective in all cases. For methods B and C an influence of ester moiety and ring size on the regioselectivity was observed. Methyl cyclopentenoate 8c gave mainly the 1,2/1,2-product regardless the allylation method while tert-butyl and benzyl ester moieties favored the 1,4-products. For larger rings 9, 10 and the anellated system 19 methods B and C behave complementary depending on the ester function: Method B gave best results of 1,4-addition products for benzyl esters while method C worked better for tert-butyl esters. Thieme Stuttgart.

Asymmetric Synthesis of (-)-(1R,2S)-Cispentacin and Related cis- and trans-2-Amino Cyclopentane- and Cyclohexane-1-carboxylic Acids

The antifungal antibiotic (-)-(1R,2S)-2-aminocyclopentane-1-carboxylic acid (cispentacin) 8 and its cyclohexane homologue 14 have been prepared utilizing the highly stereoselective conjugate addition of homochiral lithium N-benzyl-N-α-methylbenzylamide 5.