Catalyst-Directed Diastereo- and Site-Selectivity in Successive Nucleophilic and Electrophilic Allylations of Chiral 1,3-Diols: Protecting-Group-Free Synthesis of Substituted Pyrans

Inji Shin; Gang Wang; Michael J. Krische

doi:10.1002/chem.201404065

Catalyst-Directed Diastereo- and Site-Selectivity in Successive Nucleophilic and Electrophilic Allylations of Chiral 1,3-Diols: Protecting-Group-Free Synthesis of Substituted Pyrans

Inji Shin
, Gang Wang
, Michael J. Krische

Dept. of Fine Chemistry

University of Texas at Austin

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

56 Scopus citations

Abstract

The iridium-catalyzed, protecting group-free synthesis of 4-hydroxy-2,6-cis- or trans-pyrans through successive nucleophilic and electrophilic allylations of chiral 1,3-diols occurs with complete levels of catalyst-directed diastereoselectivity in the absence of protecting groups, premetallated reagents, or discrete alcohol-to-aldehyde redox reactions.

Original language	English
Pages (from-to)	13382-13389
Number of pages	8
Journal	Chemistry - A European Journal
Volume	20
Issue number	41
DOIs	https://doi.org/10.1002/chem.201404065
State	Published - 1 Oct 2014

Keywords

catalyst-directed diastereoselectivity
polyketides
protecting group-free reactions
pyran
transfer hydrogenation

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10.1002/chem.201404065

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title = "Catalyst-Directed Diastereo- and Site-Selectivity in Successive Nucleophilic and Electrophilic Allylations of Chiral 1,3-Diols: Protecting-Group-Free Synthesis of Substituted Pyrans",

abstract = "The iridium-catalyzed, protecting group-free synthesis of 4-hydroxy-2,6-cis- or trans-pyrans through successive nucleophilic and electrophilic allylations of chiral 1,3-diols occurs with complete levels of catalyst-directed diastereoselectivity in the absence of protecting groups, premetallated reagents, or discrete alcohol-to-aldehyde redox reactions.",

keywords = "catalyst-directed diastereoselectivity, polyketides, protecting group-free reactions, pyran, transfer hydrogenation",

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

note = "Publisher Copyright: {\textcopyright} 2014 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim.",

year = "2014",

month = oct,

day = "1",

doi = "10.1002/chem.201404065",

language = "English",

volume = "20",

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journal = "Chemistry - A European Journal",

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Catalyst-Directed Diastereo- and Site-Selectivity in Successive Nucleophilic and Electrophilic Allylations of Chiral 1,3-Diols: Protecting-Group-Free Synthesis of Substituted Pyrans. / Shin, Inji; Wang, Gang; Krische, Michael J.
In: Chemistry - A European Journal, Vol. 20, No. 41, 01.10.2014, p. 13382-13389.

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

TY - JOUR

T1 - Catalyst-Directed Diastereo- and Site-Selectivity in Successive Nucleophilic and Electrophilic Allylations of Chiral 1,3-Diols

T2 - Protecting-Group-Free Synthesis of Substituted Pyrans

AU - Shin, Inji

AU - Wang, Gang

AU - Krische, Michael J.

PY - 2014/10/1

Y1 - 2014/10/1

N2 - The iridium-catalyzed, protecting group-free synthesis of 4-hydroxy-2,6-cis- or trans-pyrans through successive nucleophilic and electrophilic allylations of chiral 1,3-diols occurs with complete levels of catalyst-directed diastereoselectivity in the absence of protecting groups, premetallated reagents, or discrete alcohol-to-aldehyde redox reactions.

AB - The iridium-catalyzed, protecting group-free synthesis of 4-hydroxy-2,6-cis- or trans-pyrans through successive nucleophilic and electrophilic allylations of chiral 1,3-diols occurs with complete levels of catalyst-directed diastereoselectivity in the absence of protecting groups, premetallated reagents, or discrete alcohol-to-aldehyde redox reactions.

KW - catalyst-directed diastereoselectivity

KW - polyketides

KW - protecting group-free reactions

KW - pyran

KW - transfer hydrogenation

UR - https://www.scopus.com/pages/publications/84941032064

U2 - 10.1002/chem.201404065

DO - 10.1002/chem.201404065

M3 - Article

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AN - SCOPUS:84941032064

SN - 0947-6539

VL - 20

SP - 13382

EP - 13389

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 41

ER -

Catalyst-Directed Diastereo- and Site-Selectivity in Successive Nucleophilic and Electrophilic Allylations of Chiral 1,3-Diols: Protecting-Group-Free Synthesis of Substituted Pyrans

Abstract

Keywords

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