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Novel asymmetric oxy‐michael addition reaction of the chiral ketones to the achiral γ‐ or δ‐hydroxy‐α,β‐unsaturated carbonyl compounds
Author(s) -
Watanabe Hidenori,
Machida Kaori,
Itoh Daisuke,
Nagatsuka Haruki,
Kitahara Takeshi
Publication year - 2001
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.1048
Subject(s) - chemistry , michael reaction , stereoselectivity , acetal , hemiacetal , intramolecular force , chirality (physics) , addition reaction , stereochemistry , asymmetric induction , alkoxide , enantioselective synthesis , catalysis , organic chemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
A novel asymmetric oxy‐Michael addition reaction was developed. In the presence of a catalytic amount of base, chiral ketones 1 and 2 , derived from D ‐glucose and D ‐fructose, respectively, reacted with ω‐hydroxy enones or enoates 3a–e, 17 and 21 to form the hemiacetal‐derived alkoxide which underwent stereoselective intramolecular Michael addition to give cyclic acetals. Although the stereoselectivities in the formation of the five‐membered acetal rings were modest, six‐membered ring formation proceeded with high stereoselectivity and the utility of the reaction was demonstrated by a simple syntheses of natural products. Chirality 13:379–385, 2001. © 2001 Wiley‐Liss, Inc.