Concepedia

Highly enantioselective synthesis of a chiral 3-quinolylalkanol by an asymmetric autocatalytic reaction

Takanori Shibata, Kaori Choji, Hiroshi Morioka, Tadakatsu Hayase, Kenso Soai

Chemical Communications · 1996 · 67 citations · 6 references

DOI

Concepts

Abstract

A catalytic amount of a chiral zinc alkoxide of 2-methyl-1-(3-quinolyl)propan-1-ol catalyses the enantioselective alkylation of quinoline-3-carbaldehyde by diisopropylzinc to afford 2-methyl-1-(3-quinolyl)propan-1-ol with the same configuration in high ee (up to 94%).

References

6

High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids

Ikuko I. Ohtani, Takenori Kusumi, Yoel Kashman et al. · Journal of the American Chemical Society · 1991 · 3.2K citations

, , +5

Enantioselective Addition of Organometallic Reagents to Carbonyl Compounds: Chirality Transfer, Multiplication, and Amplification

Ryōji Noyori, Masato Kitamura · Angewandte Chemie International Edition in English · 1991 · 1.2K citations

, , +12

Nitrogen Donors in Organometallic Chemistry and Homogeneous Catalysis

Antonio Togni, Luigi M. Venanzi · Angewandte Chemie International Edition in English · 1994 · 683 citations

, , +11

Highly Enantioselective Catalytic Asymmetric Automultiplication of Chiral Pyrimidyl Alcohol

Takanori Shibata, Hiroshi Morioka, Tadakatsu Hayase et al. · Journal of the American Chemical Society · 1996 · 209 citations

, , +8

The role of the product in asymmetric carbon-carbon bond formation: stoichiometric and catalytic enantioselective autoinduction

Albert H. Alberts, Hans Wynberg · Journal of the American Chemical Society · 1989 · 138 citations

, , +13