Stereodefined Acyclic Polysubstituted Silyl Ketene Aminals: Asymmetric Formation of Aldol Products with Quaternary Carbon Stereocenters: Asymmetric Formation of Aldol Products with Quaternary Carbon Stereocenters

Zackaria Nairoukh; Ilan Marek

doi:10.1002/anie.201507209

Stereodefined Acyclic Polysubstituted Silyl Ketene Aminals: Asymmetric Formation of Aldol Products with Quaternary Carbon Stereocenters: Asymmetric Formation of Aldol Products with Quaternary Carbon Stereocenters

Zackaria Nairoukh, Ilan Marek

Technion - Israel Institute of Technology

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

Abstract

The regio- and stereoselective formation of stereodefined polysubstituted silyl ketene aminals is easily achieved through selective combined carbometalation-oxidation-silylation reactions. These substrates are ideal candidates for Mukaiyama aldol reactions with aliphatic aldehydes as they give the aldol products with a quaternary carbon stereocenter α to the carbonyl groups in outstanding diastereoselectivities.

Original language	English
Pages (from-to)	14393-14397
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	54
Issue number	48
DOIs	https://doi.org/10.1002/anie.201507209
State	Published - 23 Nov 2015

Keywords

Mukaiyama reaction
aldols
one-pot reactions
quaternary carbon stereocenters
silyl ketene aminals

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry

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title = "Stereodefined Acyclic Polysubstituted Silyl Ketene Aminals: Asymmetric Formation of Aldol Products with Quaternary Carbon Stereocenters: Asymmetric Formation of Aldol Products with Quaternary Carbon Stereocenters",

abstract = "The regio- and stereoselective formation of stereodefined polysubstituted silyl ketene aminals is easily achieved through selective combined carbometalation-oxidation-silylation reactions. These substrates are ideal candidates for Mukaiyama aldol reactions with aliphatic aldehydes as they give the aldol products with a quaternary carbon stereocenter α to the carbonyl groups in outstanding diastereoselectivities.",

keywords = "Mukaiyama reaction, aldols, one-pot reactions, quaternary carbon stereocenters, silyl ketene aminals",

author = "Zackaria Nairoukh and Ilan Marek",

note = "Publisher Copyright: {\textcopyright} 2015 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim.",

year = "2015",

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doi = "10.1002/anie.201507209",

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Stereodefined Acyclic Polysubstituted Silyl Ketene Aminals: Asymmetric Formation of Aldol Products with Quaternary Carbon Stereocenters: Asymmetric Formation of Aldol Products with Quaternary Carbon Stereocenters. / Nairoukh, Zackaria; Marek, Ilan.
In: Angewandte Chemie - International Edition, Vol. 54, No. 48, 23.11.2015, p. 14393-14397.

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

TY - JOUR

T1 - Stereodefined Acyclic Polysubstituted Silyl Ketene Aminals: Asymmetric Formation of Aldol Products with Quaternary Carbon Stereocenters

T2 - Asymmetric Formation of Aldol Products with Quaternary Carbon Stereocenters

AU - Nairoukh, Zackaria

AU - Marek, Ilan

PY - 2015/11/23

Y1 - 2015/11/23

N2 - The regio- and stereoselective formation of stereodefined polysubstituted silyl ketene aminals is easily achieved through selective combined carbometalation-oxidation-silylation reactions. These substrates are ideal candidates for Mukaiyama aldol reactions with aliphatic aldehydes as they give the aldol products with a quaternary carbon stereocenter α to the carbonyl groups in outstanding diastereoselectivities.

AB - The regio- and stereoselective formation of stereodefined polysubstituted silyl ketene aminals is easily achieved through selective combined carbometalation-oxidation-silylation reactions. These substrates are ideal candidates for Mukaiyama aldol reactions with aliphatic aldehydes as they give the aldol products with a quaternary carbon stereocenter α to the carbonyl groups in outstanding diastereoselectivities.

KW - Mukaiyama reaction

KW - aldols

KW - one-pot reactions

KW - quaternary carbon stereocenters

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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ER -

Stereodefined Acyclic Polysubstituted Silyl Ketene Aminals: Asymmetric Formation of Aldol Products with Quaternary Carbon Stereocenters: Asymmetric Formation of Aldol Products with Quaternary Carbon Stereocenters

Abstract

Keywords

All Science Journal Classification (ASJC) codes

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