Top > Search of International Patents > Process of making alpha -aminooxyketone/alpha -aminooxyaldehyde and alpha -hydroxyketone/alpha -hydroxyaldehyde compounds and a process making reaction products from cyclic alpha ,beta -unsaturated ketone substrates and nitroso substrates

Process of making alpha -aminooxyketone/alpha -aminooxyaldehyde and alpha -hydroxyketone/alpha -hydroxyaldehyde compounds and a process making reaction products from cyclic alpha ,beta -unsaturated ketone substrates and nitroso substrates

Foreign code F110003522
File No. B12-03WO
Posted date Jun 28, 2011
Country United States of America
Application number 50659006
Gazette No. 20070037973
Gazette No. 07872123
Date of filing Aug 18, 2006
Gazette Date Feb 15, 2007
Gazette Date Jan 18, 2011
International application number PCT/US2005/005426
Date of international filing Feb 18, 2005
Priority data
  • P2004-044540 (Feb 20, 2004) JP
Title Process of making alpha -aminooxyketone/alpha -aminooxyaldehyde and alpha -hydroxyketone/alpha -hydroxyaldehyde compounds and a process making reaction products from cyclic alpha ,beta -unsaturated ketone substrates and nitroso substrates
Abstract The present invention is directed to a process of making alpha -aminooxyketone and alpha -hydroxyketone compounds. The synthetic pathway involves reacting an aldehyde or ketone substrate and a nitroso substrate in the presence of a catalyst of the formula (IV):wherein Xa-Xc represent independently nitrogen, carbon, oxygen or sulfur and Z represents a 4 to 10-membered ring with or without a substituent and optionally a further step to convert the alpha -aminooxyketone compound formed to the alpha -hydroxyketone compound which results in alpha -aminooxyketone and alpha -hydroxyketone compounds with high enantioselectivity and high purity. The present invention is also directed to a catalytic asymmetric O-nitroso Aldol/Michael reaction involving a cyclic alpha ,beta -unsaturated ketone substrate and a nitroso substrate. This methodology involves reacting the cyclic alpha ,beta -unsaturated ketone substrate and the nitroso substrate in the presence of a proline-based catalyst, to provide a heterocyclic product.
  • Inventor, and Inventor/Applicant
  • Momiyama, Norie; Sendai [JP]
  • Torii, Hiromi; Kariya [JP]
  • Saito, Susumu; Nagoya [JP]
  • Yamamoto, Hisashi; Chicago IL [US]
  • Yamamoto, Yuhei; Tsukuba [JP]
  • Japan Science And Technology Agency, Saitama [JP]
IPC(International Patent Classification)
Reference ( R and D project ) SORST Selected in Fiscal 2000
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