75947-27-2

Upstream product

• 75909-37-4 (S)-(E)-1-(O-methylmandeloxy)butadiene 
• 107-02-8 acrolein 
• 121840-89-9 (+/-)-(E)-1-(2-methoxy-2-phenylacetoxy)-1,3-butadiene 
• 139157-56-5 (R)-Methoxy-phenyl-acetic acid (1R,2S,3R,5R,6S)-tricyclo[4.2.1.0^2,5]non-7-en-3-yl ester 
• 26164-26-1 (S)-2-methoxy-2-phenylacetic acid 
• 139157-56-5 Methoxy-phenyl-acetic acid (1R,2S,5R,6S)-tricyclo[4.2.1.0^2,5]non-7-en-3-yl ester 

Downstream Products

• 27583-43-3 2-(hydroxymethyl)cyclohexanol 
• 51606-50-9 (1R,2R)-2-(hydroxymethyl)cyclohexanol 

Relevant academic research and scientific papers

Diels-Alder reactions with dienes bearing a remote stereogenic center. Conformational model for diastereofacial selectivity

In Diels-Alder reactions of 1-acyloxydienes, the 1-O-methylmandeloxy group has the distinct advantage of serving dual functions. Not only is it an effective chiral auxiliary for Diels-Alder stereocontrol, but also it provides rather reliable determination of the absolute stereochemistry of the Diels-Alder adduct, via the Dale-Mosher NMR model, subject only to the ability to resolve the proper NMR resonances. Study of the Diels-Alder reactions of such chiral 1-acyloxydienes has led us to a transition structure model which uniquely explains the origin of the observed stereoselectivities and is supported by experimental evidence, including X-ray structures showing the conformations of three Diels-Alder adducts. The model may also have wider applicability in conformational analysis and control of selectivity in other reactions.

CONFORMATIONAL MODEL FOR ASYMMETRIC DIELS-ALDER REACTIONS WITH CHIRAL DIENES

1-(O-methylmandeloxy)dienes have significant advantages for asymmetric Diels-Alder reactions, and we now show that high (>90percent) diastereofacial selectivities can be obtained with these dienes, permitting considerable choice as to dienophile and the p