66511-82-8

Upstream product

• 6909-30-4 (1S,2R,4R)-limonene-1,2-epoxide 
• 200437-33-8 (1S,2S,5R)-2-azido-2-methyl-5?(prop-1-en-2-yl)cyclohexanol 
• 5989-27-5 D-limonene 
• 1195-92-2 (4R)-limonene 1,2-epoxide 

Downstream Products

• 72552-28-4 (1S,2S,5R)-5-Isopropenyl-2-methoxy-2-methyl-cyclohexylamine 

Relevant academic research and scientific papers

Chiral amino and imino-alcohols based on (R)-limonene

Derivatives of the natural occurring and inexpensive terpene (R)-limonene were synthetized and completely characterized. Starting from internal olefin epoxidation, followed by epoxide opening with sodium azide and azide reduction with LiAlH4, two chiral amino-alcohols were obtained. The amino-alcohols were reacted with three different aldehydes, generating six new imino-alcohols, two of them yielding crystals suitable for X-ray diffraction characterization. The reduction of four of these compounds with LiAlH4 led to new amino-alcohols. All derivatives were obtained with good overall yields through simple reaction protocols.

Enantioselective alkynylations of aromatic and aliphatic aldehydes catalyzed by terpene derived chiral amino alcohols

Enantioselective alkynyl zinc additions to aromatic and aliphatic aldehydes have been studied using terpene derived chiral amino alcohol ligands. The limonene derived amino alcohol (1R,2R,5S)-2-methyl-5-(1-methylethenyl)-2-(1- pyrrolidinyl)cyclohexanol ga