Asymmetric iridium-catalyzed C–C coupling of chiral diols via site-selective redox-triggered carbonyl addition

Inji Shin; Michael J. Krische

doi:10.1007/128_2015_651

Asymmetric iridium-catalyzed C–C coupling of chiral diols via site-selective redox-triggered carbonyl addition

Inji Shin
, Michael J. Krische

Dept. of Fine Chemistry

University of Texas at Austin

Research output: Contribution to journal › Article › peer-review

22 Scopus citations

Abstract

Cyclometalated π-allyliridium C,O-benzoate complexes modified by axially chiral chelating phosphine ligands display a pronounced kinetic preference for primary alcohol dehydrogenation, enabling highly site-selective redox-triggered carbonyl additions of chiral primary-secondary 1,3-diols with exceptional levels of catalyst-directed diastereoselectivity. Unlike conventional methods for carbonyl allylation, the present redox-triggered alcohol C–H functionalizations bypass the use of protecting groups, premetalated reagents, and discrete alcohol-to-aldehyde redox reactions.

Original language	English
Pages (from-to)	85-101
Number of pages	17
Journal	Topics in Current Chemistry
Volume	372
DOIs	https://doi.org/10.1007/128_2015_651
State	Published - 2015

Keywords

Allylation
Dehydrogenation
Diastereoselectivity
Enantioselectivity
Green chemistry
Iridium
Polyketides
Transfer hydrogenation

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10.1007/128_2015_651

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title = "Asymmetric iridium-catalyzed C–C coupling of chiral diols via site-selective redox-triggered carbonyl addition",

abstract = "Cyclometalated π-allyliridium C,O-benzoate complexes modified by axially chiral chelating phosphine ligands display a pronounced kinetic preference for primary alcohol dehydrogenation, enabling highly site-selective redox-triggered carbonyl additions of chiral primary-secondary 1,3-diols with exceptional levels of catalyst-directed diastereoselectivity. Unlike conventional methods for carbonyl allylation, the present redox-triggered alcohol C–H functionalizations bypass the use of protecting groups, premetalated reagents, and discrete alcohol-to-aldehyde redox reactions.",

keywords = "Allylation, Dehydrogenation, Diastereoselectivity, Enantioselectivity, Green chemistry, Iridium, Polyketides, Transfer hydrogenation",

author = "Inji Shin and Krische, \{Michael J.\}",

note = "Publisher Copyright: {\textcopyright} Springer International Publishing Switzerland 2015.",

year = "2015",

doi = "10.1007/128\_2015\_651",

language = "English",

volume = "372",

pages = "85--101",

journal = "Topics in Current Chemistry",

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T1 - Asymmetric iridium-catalyzed C–C coupling of chiral diols via site-selective redox-triggered carbonyl addition

AU - Shin, Inji

AU - Krische, Michael J.

N1 - Publisher Copyright: © Springer International Publishing Switzerland 2015.

PY - 2015

Y1 - 2015

N2 - Cyclometalated π-allyliridium C,O-benzoate complexes modified by axially chiral chelating phosphine ligands display a pronounced kinetic preference for primary alcohol dehydrogenation, enabling highly site-selective redox-triggered carbonyl additions of chiral primary-secondary 1,3-diols with exceptional levels of catalyst-directed diastereoselectivity. Unlike conventional methods for carbonyl allylation, the present redox-triggered alcohol C–H functionalizations bypass the use of protecting groups, premetalated reagents, and discrete alcohol-to-aldehyde redox reactions.

AB - Cyclometalated π-allyliridium C,O-benzoate complexes modified by axially chiral chelating phosphine ligands display a pronounced kinetic preference for primary alcohol dehydrogenation, enabling highly site-selective redox-triggered carbonyl additions of chiral primary-secondary 1,3-diols with exceptional levels of catalyst-directed diastereoselectivity. Unlike conventional methods for carbonyl allylation, the present redox-triggered alcohol C–H functionalizations bypass the use of protecting groups, premetalated reagents, and discrete alcohol-to-aldehyde redox reactions.

KW - Allylation

KW - Dehydrogenation

KW - Diastereoselectivity

KW - Enantioselectivity

KW - Green chemistry

KW - Iridium

KW - Polyketides

KW - Transfer hydrogenation

UR - https://www.scopus.com/pages/publications/84959333707

U2 - 10.1007/128_2015_651

DO - 10.1007/128_2015_651

M3 - Article

C2 - 26187028

AN - SCOPUS:84959333707

SN - 0340-1022

VL - 372

SP - 85

EP - 101

JO - Topics in Current Chemistry

JF - Topics in Current Chemistry

ER -

Asymmetric iridium-catalyzed C–C coupling of chiral diols via site-selective redox-triggered carbonyl addition

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Keywords

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