Catalytic Enantioselective Allylations of Acetylenic Aldehydes via 2‑Propanol-Mediated Reductive Coupling

Cyclometalated π-allyliridium C,O-benzoates modified by (S)-SEGPHOS or (S)-Cl,OMe-BIPHEP catalyze enantioselective 2-propanol-mediated reductive couplings of diverse nonmetallic allyl pronucleophiles with the acetylenic aldehyde TIPSCCCHO. Absolute stereochemistries of the resulting secondary homoa...

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Published inOrganic letters Vol. 20; no. 13; pp. 4144 - 4147
Main Authors Brito, Gilmar A, Della-Felice, Franco, Luo, Guoshun, Burns, Alexander S, Pilli, Ronaldo A, Rychnovsky, Scott D, Krische, Michael J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.07.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNCTIONALIZATION
ASYMMETRIC ALLYLATIONS
REAGENTS
ABSOLUTE-CONFIGURATION
STEREOSELECTIVITY
KINETIC RESOLUTION
CARBONYL ALLYLATION
PROPARGYLIC ALCOHOLS
ACETATE
OXIDATION LEVEL
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Summary:Cyclometalated π-allyliridium C,O-benzoates modified by (S)-SEGPHOS or (S)-Cl,OMe-BIPHEP catalyze enantioselective 2-propanol-mediated reductive couplings of diverse nonmetallic allyl pronucleophiles with the acetylenic aldehyde TIPSCCCHO. Absolute stereochemistries of the resulting secondary homoallylic–propargylic alcohols were assigned using Rychnovsky’s competing enantioselective conversion method.
Bibliography:FAPESP
National Science Foundation
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b01776