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• W2024197949 endingPage "12769" @default.
• W2024197949 startingPage "12764" @default.
• W2024197949 abstract "Abstract A flexible approach, applicable on a gram scale, to chiral 2‐ endo ‐substituted 9‐oxabispidines was developed. The key intermediate, a cis ‐configured 6‐aminomethylmorpholine‐2‐carbonitrile, was prepared from ( R )‐3‐aminopropane‐1,2‐diol and 2‐chloroacrylonitrile. The 2‐ endo substituent was introduced by Grignard addition, cyclization, and exo ‐selective reduction, thus furnishing the enantiomerically pure bi‐ and tricyclic 9‐oxabispidines in 19–59 % yield. The CuCl 2 complex of the tricyclic 9‐oxabispidine, which carries an 2‐ endo ,N‐anellated piperidine ring, is an excellent catalyst for enantioselective Henry reactions giving the S ‐configured β‐nitro alcohols in 91–98 % ee (13 examples). Surprisingly, the analogous copper complexes of the bicyclic 9‐oxabispidines delivered the enantiocomplementary R ‐configured products in 33–57 % ee . The respective transition states were discussed." @default.
• W2024197949 created "2016-06-24" @default.
• W2024197949 creator A5002216983 @default.
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• W2024197949 creator A5054638656 @default.
• W2024197949 creator A5086028523 @default.
• W2024197949 date "2009-11-18" @default.
• W2024197949 modified "2023-10-18" @default.
• W2024197949 title "Chiral 2-<i>endo</i>-Substituted 9-Oxabispidines: Novel Ligands for Enantioselective Copper(II)-Catalyzed Henry Reactions" @default.
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• W2024197949 doi "https://doi.org/10.1002/chem.200901789" @default.
• W2024197949 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/19834941" @default.
• W2024197949 hasPublicationYear "2009" @default.

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