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Rational Design of a Metallocatalytic Cavitand for Regioselective Hydration of Specific Alkynes
Author(s) -
Endo Naoki,
Inoue Mami,
Iwasawa Tetsuo
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701613
Subject(s) - cavitand , chemistry , supramolecular chemistry , moiety , regioselectivity , substrate (aquarium) , stereochemistry , rational design , folding (dsp implementation) , molecule , supramolecular assembly , catalysis , combinatorial chemistry , organic chemistry , nanotechnology , oceanography , materials science , engineering , electrical engineering , geology
The synthesis of a functionalized supramolecular cavitand with inwardly oriented Au I and P=O moieties was explored, including its catalytic proclivity in the selective hydration of internal alkynes. The cavitand works as a supramolecular flask device: Au I coordinates to the triple bond, the P=O moiety connects with a H 2 O molecule, and the cavity favors folding of a single alkynyl side chain. Several tests of different substrate patterns indicated that the cavity was substrate specific, similar to enzymatic catalysis.