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A Borate Propeller Compound as Chiral Catalyst for an Asymmetrically Induced Diels‐Alder Reaction
Author(s) -
Kaufmann Dieter,
Boese Roland
Publication year - 1990
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199005451
Subject(s) - methacrolein , enantioselective synthesis , cyclopentadiene , borane , diels–alder reaction , catalysis , chemistry , propeller , boron , adduct , molecule , optically active , organic chemistry , polymer , monomer , marine engineering , engineering , methacrylic acid
Three binaphthyl groups as “blades” have been joined together to give the propeller compound 1 . The synthesis of this compound proved surprisingly easy via reaction of a borane with optically active 1,1′‐bi‐2‐naphthol. Compound 1 is more than just “a cute molecule”; it also catalyzes a highly exo and enantioselective Diels–Alder reaction of cyclopentadiene with methacrolein.