Enantioselective Michael Addition of Water

نویسندگان

  • Bi-Shuang Chen
  • Verena Resch
  • Linda G Otten
  • Ulf Hanefeld
چکیده

The enantioselective Michael addition using water as both nucleophile and solvent has to date proved beyond the ability of synthetic chemists. Herein, the direct, enantioselective Michael addition of water in water to prepare important β-hydroxy carbonyl compounds using whole cells of Rhodococcus strains is described. Good yields and excellent enantioselectivities were achieved with this method. Deuterium labeling studies demonstrate that a Michael hydratase catalyzes the water addition exclusively with anti-stereochemistry.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Chiral-Sc catalyzed asymmetric Michael addition/protonation of thiols with enones in water.

Asymmetric Michael reactions and enantioselective protonations between enones and thiols were catalyzed by a Sc(OTf)(3)-chiral 2,2'-bipyridine complex in water. The remarkable governing of the enantioselectivity for simple introduction of protons despite their abnormally high mobility in water may provide us with new synthetic opportunities as well as significant chemical advances.

متن کامل

Convenient One-pot Access to Pyrano[2,3-d]pyrimidine Derivatives via a CuCl2.2H2O Catalyzed Knoevenagel-Michael Addition Reaction in Water/Ethanol Media

Convenient procedure for the synthesis of corresponding pyrano[2,3-d]pyrimidine derivatives were developed via one-pot three-component reaction of aryl aldehyde derivatives, malononitrile with barbituric acids in the presence of copper (II) chloride dihydrate (CuCl2.2H2O) as highly efficient Lewis acid catalyst. This protocol has advantages such as readily and inexpensive catalyst, high reactio...

متن کامل

Hydrogen bonding mediated enantioselective organocatalysis in brine: significant rate acceleration and enhanced stereoselectivity in enantioselective Michael addition reactions of 1,3-dicarbonyls to β-nitroolefins.

Brine provides remarkable rate acceleration and a higher level of stereoselectivity over organic solvents, due to the hydrophobic hydration effect, in the enantioselective Michael addition reactions of 1,3-dicarbonyls to β-nitroolefins using chiral H-donors as organocatalysts.

متن کامل

Enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes catalyzed by binaphthyl-derived organocatalysts

The highly enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes, promoted by binaphthyl-modified chiral bifunctional organocatalysts is described. This reaction afforded the chiral functionalized naphthoquinones in high yields (81-95%) and excellent enantioselectivities (91-98% ee) under low catalyst loading (1 mol %).

متن کامل

Simple chiral sulfonamide primary amine catalysed highly enantioselective Michael addition of malonates to enones.

A chiral sulfonamide primary amine-organocatalysed, highly enantioselective Michael addition of malonates to enones has been developed. This reaction afforded the corresponding products in excellent yields (up to 99%) and excellent enantioselectivity (up to 99% ee).

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:

دوره 21  شماره 

صفحات  -

تاریخ انتشار 2015