Preparation of Macrocyclic Z-Enoates and (E,Z)- or (Z,E)-Dienoates through Catalytic Stereoselective Ring-Closing Metathesis | Zendy

Hanmo Zhang | Zendy; Elsie C. Yu | Zendy; Sebastian Torker | Zendy; Richard R. Schrock | Zendy; Amir H. Hoveyda | Zendy

Open Access

Preparation of Macrocyclic Z-Enoates and (E,Z)- or (Z,E)-Dienoates through Catalytic Stereoselective Ring-Closing Metathesis

Author(s) -

Hanmo Zhang,

Elsie C. Yu,

Sebastian Torker,

Richard R. Schrock,

Amir H. Hoveyda

Publication year - 2014

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja510768c

Subject(s) - chemistry , stereoselectivity , ring closing metathesis , catalysis , metathesis , closing (real estate) , ring (chemistry) , stereochemistry , organic chemistry , polymerization , polymer , political science , law

The first examples of catalyst-controlled stereoselective macrocyclic ring-closing metathesis reactions that generate Z-enoates as well as (E,Z)- or (Z,E)-dienoates are disclosed. Reactions promoted by 3.0-10 mol % of a Mo-based monoaryloxide pyrrolide complex proceed to completion within 2-6 h at room temperature. The desired macrocycles are formed in 79:21 to >98:2 Z/E selectivity; stereoisomerically pure products can be obtained in 43-75% yield after chromatography. Utility is demonstrated by application to a concise formal synthesis of the natural product (+)-aspicilin.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research