160865-72-5

Upstream product

• 2216-51-5 (-)-menthol 
• 102-92-1 cinnamoyl chloride 
• 108945-28-4 (1S,2R,5S)‐2‐isopropyl‐5‐methylcyclohexyl acrylate 
• 100-51-6 benzyl alcohol 

Downstream Products

• 114466-84-1 (2R,3R)-(+)-menthyl 2-amino-3-((S-3-nitro-2-pyridinesulfenyl)thio)-3-phenylpropionate 
• 114466-85-2 (2R,3R)-2-((tert-butyloxycarbonyl)amino)-3-((S-3-nitro-2-pyridinesulfenyl)thio)-3-phenylpropionic acid 
• 114529-89-4 (2R,3R)-(+)-menthyl 2-amino-3-((4-methoxybenzyl)thio)-3-phenylpropionate 
• 114529-88-3 cis-(2S,3S)-2-((+)-menthyloxycarbonyl)-3-phenylaziridine 

Relevant academic research and scientific papers

Mizoroki-Heck Reaction of Unstrained Aryl Ketones via Ligand-Promoted C-C Bond Olefination

Mizoroki-Heck reaction of unstrained aryl ketone with acrylate/styrene is accomplished via palladium-catalyzed ligand-promoted C-C bond cleavage. Various (hetero)aryl ketones are compatible in the reaction, affording the alkene product in good to excellent yields. Further applications in the late-stage olefination of some drugs, natural products, and fragrance-derived aryl ketones demonstrate the synthetic utility of this protocol. By employing ketone as both the directing group and the leaving group, 1,2-bifunctionalization is achieved via sequential ortho-C-H alkylation/ipso-Heck olefination.

Selective Construction of C?C and C=C Bonds by Manganese Catalyzed Coupling of Alcohols with Phosphorus Ylides

Herein, we report the manganese catalyzed coupling of alcohols with phosphorus ylides. The selectivity in the coupling of primary alcohols with phosphorus ylides to form carbon-carbon single (C?C) and carbon-carbon double (C=C) bonds can be controlled by the ligands. In the conversion of more challenging secondary alcohols with phosphorus ylides the selectivity towards the formation of C?C vs. C=C bonds can be controlled by the reaction conditions, namely the amount of base. The scope and limitations of the coupling reactions were thoroughly evaluated by the conversion of 21 alcohols and 15 ylides. Notably, compared to existing methods, which are based on precious metal complexes as catalysts, the present catalytic system is based on earth abundant manganese catalysts. The reaction can also be performed in a sequential one-pot reaction generating the phosphorus ylide in situ followed manganese catalyzed C?C and C=C bond formation. Mechanistic studies suggest that the C?C bond was generated via a borrowing hydrogen pathway and the C=C bond formation followed an acceptorless dehydrogenative coupling pathway. (Figure presented.).