79606-79-4

Upstream product

• 77903-42-5 2-tert-Butyl-2-trimethylsilanyloxy-cyclopropanecarboxylic acid methyl ester 
• 100-52-7 benzaldehyde 
• 75-11-6 diiodomethane 
• 55107-14-7 Methyl 4,4-dimethyl-3-oxopentanoate 

Downstream Products

• 124645-64-3 methyl 2-(1-oxo-1-phenyl-methyl)-5,5-dimethyl-4-oxo-hexanoate 
• 102536-77-6 methyl c-5-allyl-t-5-tert-butyl-t-2-phenyl-tetrahydrofuran-r-3-carboxylate 
• 124645-65-4 methyl 5-tert-butyl-2-phenyl-furan-3-carboxylate 
• 124645-63-2 methyl 5-tert-butyl-t-2-phenyl-2,3-dihydrofuran-r-3-carboxylate 
• 124645-56-3 methyl c-5-tert-butyl-c-2-phenyl-tetrahydrofuran-r-3-carboxylate 
• 102536-79-8 methyl t-5-tert-butyl-c-5-cyano-c-2-phenyl-tetrahydrofuran-r-3-carboxylate 
• 102536-79-8 methyl c-5-tert-butyl-t-5-cyano-c-2-phenyl-tetrahydrofuran-r-3-carboxylate 
• 665006-23-5 methyl 1-benzyl-5-tert-butyl-2-phenyl-1H-pyrrole-3-carboxylate 
• 875918-24-4 5-tert-butyl-3-(methoxycarbonyl)-1-(2-methylpropyl)-2-phenylpyrrole 
• 875918-49-3 5-tert-butyl-3-(methoxycarbonyl)-2-phenylthiophene 
• 102536-77-6 methyl t-5-allyl-c-5-tert-butyl-c-2-phenyl-tetrahydrofuran-r-3-carboxylate 

Relevant academic research and scientific papers

A combined DFT and NMR investigation of the zinc organometallic intermediate proposed in the syn-selective tandem chain extension-aldol reaction of β-keto esters

The tandem chain extension-aldol (TCA) reaction of β-keto esters provides an α-substituted γ-keto ester with an average syn:anti selectivity of 10:1. It is proposed that the reaction proceeds via a carbon-zinc bound organometallic intermediate potentially bearing mechanistic similarity to the Reformatsky reaction. Evidence, derived from control Reformatsky reactions and a study of the structure of the TCA intermediate utilizing DFT methods and NMR spectroscopy, suggests the γ-keto group of the TCA intermediate plays a significant role in diastereoselectivity observed in this reaction. Such coordination effects have design implications for future zinc mediated reactions.

New pyrrole-based amino acids for the synthesis of peptidomimetic constrained scaffolds

A new family of pyrrole-based amino acids have been prepared through the microwave assisted Paal-Knorr reaction of 1-4 ketoesters derived from the corresponding β-ketoester with a functional homologation. The carboxylic group is located in position 3 of the pyrrole, whereas the amino group, protected with the Cbz moiety, is present on the side chain in positions 1 or 2. These compounds were used to prepare constrained oligopeptides.

Microwave-assisted Paal-Knorr reaction - Three-step regiocontrolled synthesis of polysubstituted furans, pyrroles and thiophenes

An efficient and highly versatile synthesis of furans, pyrroles and thiophenes is described. Starting from commercially available or easily prepared β-keto esters, functional homologation provides differently substituted 1,4-diketones that can be transfor

Microwave-Assisted Paal-Knorr Reaction. A Rapid Approach to Substituted Pyrroles and Furans

(Equation presented) An array of tetrasubstituted pyrroles (and trisubstituted furans) was obtained using a simple three-step procedure. Functional homologation of a β-ketoester with an aldehyde followed by oxidation gave a series of differently substitut

Tandem chain extension-aldol reaction: syn selectivity with a zinc enolate.

A tandem chain extension-aldol reaction was developed in which beta-keto esters are transformed to alpha-substituted-gamma-keto esters in an efficient zinc-mediated, one-pot reaction. The diastereoselectivity of the reaction ranged from good to excellent

A TITANOXYCYCLOPROPANE AS INTERMEDIATE IN A HIGHLY STEREOSELECTIVE HOMOALDOL TYPE ADDITION SYNTHESES OF CIS-SUBSTITUTED TETRAHYDROFURAN DERIVATIVES

Reaction of methyl 2-siloxycyclopropanecarboxylate 4 with TiCl4 provides the unique titanoxycyclopropane 10 whose structure could be elucidated by means of NMR-spectroscopy.Its additions to aldehydes and acetophenone occur with high stereoselectivity to a

LEWIS-ACID-PROMOTED ADDITIONS OF CARBONYL COMPOUNDS TO DONOR-ACCEPTOR SUBSTITUTED CYCLOPROPANES: A NEW SYNTHESIS OF 2,3-DIHYDROFURANE DERIVATIVES

Methyl 2,3-dihydrofurane-3-carboxylates are synthesized from siloxycyclopropaneesters and ketones in the presence of TiCl4 with good yields.