Electrophilic Oxidation of Stereodefined Polysubstituted Silyl Ketone Aminals

Jian Qiang Huang; Zackaria Nairoukh; Ilan Marek

doi:10.1002/ejoc.201701516

Electrophilic Oxidation of Stereodefined Polysubstituted Silyl Ketone Aminals

Jian Qiang Huang, Zackaria Nairoukh, Ilan Marek^*

^*Corresponding author for this work

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

4 Scopus citations

Abstract

We reported herein a practical approach to acyclic tertiary α-hydroxy carbonyl compounds in only two chemical steps from alkynes with excellent diastereoselectivity through the oxidation of stereodefined polysubstituted silyl ketone aminals. The products could be smoothly converted to synthetically useful enantiomerically enriched 1,2-diol derivatives.

Original language	American English
Pages (from-to)	614-618
Number of pages	5
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	5
DOIs	https://doi.org/10.1002/ejoc.201701516
State	Published - 7 Feb 2018
Externally published	Yes

Bibliographical note

Funding Information:
This research was supported by a grant from the European Research Council under the Seventh Framework Program of the European Community (ERC Grant Agreement 338912). I. M. is holder of the Sir Michael and Lady Sobell Academic Chair.

Publisher Copyright:
© 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

Chirality
Diols
Oxidation
Silylketone aminals
Synthetic methods
α-Hydroxy carbonyls

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10.1002/ejoc.201701516

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title = "Electrophilic Oxidation of Stereodefined Polysubstituted Silyl Ketone Aminals",

abstract = "We reported herein a practical approach to acyclic tertiary α-hydroxy carbonyl compounds in only two chemical steps from alkynes with excellent diastereoselectivity through the oxidation of stereodefined polysubstituted silyl ketone aminals. The products could be smoothly converted to synthetically useful enantiomerically enriched 1,2-diol derivatives.",

keywords = "Chirality, Diols, Oxidation, Silylketone aminals, Synthetic methods, α-Hydroxy carbonyls",

author = "Huang, {Jian Qiang} and Zackaria Nairoukh and Ilan Marek",

note = "Funding Information: This research was supported by a grant from the European Research Council under the Seventh Framework Program of the European Community (ERC Grant Agreement 338912). I. M. is holder of the Sir Michael and Lady Sobell Academic Chair. Publisher Copyright: {\textcopyright} 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

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T1 - Electrophilic Oxidation of Stereodefined Polysubstituted Silyl Ketone Aminals

AU - Huang, Jian Qiang

AU - Nairoukh, Zackaria

AU - Marek, Ilan

N1 - Funding Information: This research was supported by a grant from the European Research Council under the Seventh Framework Program of the European Community (ERC Grant Agreement 338912). I. M. is holder of the Sir Michael and Lady Sobell Academic Chair. Publisher Copyright: © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

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Y1 - 2018/2/7

N2 - We reported herein a practical approach to acyclic tertiary α-hydroxy carbonyl compounds in only two chemical steps from alkynes with excellent diastereoselectivity through the oxidation of stereodefined polysubstituted silyl ketone aminals. The products could be smoothly converted to synthetically useful enantiomerically enriched 1,2-diol derivatives.

AB - We reported herein a practical approach to acyclic tertiary α-hydroxy carbonyl compounds in only two chemical steps from alkynes with excellent diastereoselectivity through the oxidation of stereodefined polysubstituted silyl ketone aminals. The products could be smoothly converted to synthetically useful enantiomerically enriched 1,2-diol derivatives.

KW - Chirality

KW - Diols

KW - Oxidation

KW - Silylketone aminals

KW - Synthetic methods

KW - α-Hydroxy carbonyls

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DO - 10.1002/ejoc.201701516

M3 - Article

AN - SCOPUS:85041380116

SN - 1434-193X

VL - 2018

SP - 614

EP - 618

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 5

ER -

Electrophilic Oxidation of Stereodefined Polysubstituted Silyl Ketone Aminals

Abstract

Bibliographical note

Keywords

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