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2005
Hydroxylamine derivatives
Q 0110
Broensted Acid Catalysis of Achiral Enamine for Regio- and Enantioselective
Aldol Synthesis. — With the proper choice of chiral Broensted acid and en22- 067 Nitroso
amine combinations, the exclusive formation of either O- or N-nitroso aldol products
from the reaction with nitrosobenzene is realized with high enantioselectivities. Under
optimized conditions using naphthyl glycolic acid (NGA) as catalyst, cyclopentene,
cyclohexene and cycloheptene enamines derived from pyrrolidine, piperidine, and
homopiperidine afford the corresponding O-cycloalkyl hydroxylamines. By use of
TADDOL derivative TND as catalyst, cyclohexene and cycloheptene enamines derived
from piperidine, morpholine, and thiomorpholine give N-cycloalkyl hydroxylamines.
— (MOMIYAMA, N.; YAMAMOTO*, H.; J. Am. Chem. Soc. 127 (2005) 4,
1080-1081; Dep. Chem., Univ. Chicago, Chicago, IL 60637, USA; Eng.) — Klein
2005
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