10.1021/ja510768c.s001
Hanmo Zhang
Hanmo
Zhang
Elsie
C. Yu
Elsie
C.
Yu
Sebastian Torker
Sebastian
Torker
Richard R. Schrock
Richard R.
Schrock
Amir H. Hoveyda
Amir H.
Hoveyda
Preparation
of Macrocyclic <i>Z</i>‑Enoates
and (<i>E</i>,<i>Z</i>)- or (<i>Z</i>,<i>E</i>)‑Dienoates through Catalytic Stereoselective
Ring-Closing Metathesis
American Chemical Society
2015
macrocycle
Catalytic
metathesi
selectivity
utility
completion
application
MetathesisThe
chromatography
pyrrolide
stereo
Macrocyclic
Preparation
mol
Stereoselective
aspicilin
macrocyclic
room temperature
synthesis
2015-12-17 06:04:48
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Preparation_of_Macrocyclic_i_Z_i_Enoates_and_i_E_i_i_Z_i_or_i_Z_i_i_E_i_Dienoates_through_Catalytic_Stereoselective_Ring_Closing_Metathesis/2044596
The
first examples of catalyst-controlled stereoselective
macrocyclic ring-closing metathesis reactions that generate <i>Z</i>-enoates as well as (<i>E</i>,<i>Z</i>)- or (<i>Z</i>,<i>E</i>)-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 <i>Z</i>/<i>E</i> 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.