Asymmetric NHC-catalyzed aza-Diels-Alder reactions: Highly enantioselective route to α-amino acid derivatives and DFT calculations

Limin Yang; Fei Wang; Richmond Lee; Yunbo Lv; Kuo-Wei Huang; Guofu Zhong

doi:10.1021/ol501424f

Asymmetric NHC-catalyzed aza-Diels-Alder reactions: Highly enantioselective route to α-amino acid derivatives and DFT calculations

Limin Yang, Fei Wang, Richmond Lee, Yunbo Lv, Kuo-Wei Huang, Guofu Zhong

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

56 Scopus citations

Abstract

A facile N-heterocyclic carbene catalytic enantioselective aza-Diels-Alder reaction of oxodiazenes with α-chloroaldehydes as dienophile precursors is reported, with excellent enantioselectivity (ee > 99%) and excellent yield (up to 93%). DFT study showed that cis-TSa, formed from a top face approach of oxodiazene to cis-IIa, is the most favorable transition state and is consistent with the experimental observations. © 2014 American Chemical Society.

Original language	English (US)
Pages (from-to)	3872-3875
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	15
DOIs	https://doi.org/10.1021/ol501424f
State	Published - Jul 2 2014

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Physical and Theoretical Chemistry

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10.1021/ol501424f

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title = "Asymmetric NHC-catalyzed aza-Diels-Alder reactions: Highly enantioselective route to α-amino acid derivatives and DFT calculations",

abstract = "A facile N-heterocyclic carbene catalytic enantioselective aza-Diels-Alder reaction of oxodiazenes with α-chloroaldehydes as dienophile precursors is reported, with excellent enantioselectivity (ee > 99%) and excellent yield (up to 93%). DFT study showed that cis-TSa, formed from a top face approach of oxodiazene to cis-IIa, is the most favorable transition state and is consistent with the experimental observations. {\textcopyright} 2014 American Chemical Society.",

author = "Limin Yang and Fei Wang and Richmond Lee and Yunbo Lv and Kuo-Wei Huang and Guofu Zhong",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: We thank the NSFC (21302032 and 21373073) and the PCSIRT (IRT 1231) for financial support. G.Z. appreciates a QjanJiang Scholar from Zhejiang Province in China.",

year = "2014",

month = jul,

day = "2",

doi = "10.1021/ol501424f",

language = "English (US)",

volume = "16",

pages = "3872--3875",

journal = "Organic Letters",

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T1 - Asymmetric NHC-catalyzed aza-Diels-Alder reactions: Highly enantioselective route to α-amino acid derivatives and DFT calculations

AU - Yang, Limin

AU - Wang, Fei

AU - Lee, Richmond

AU - Lv, Yunbo

AU - Huang, Kuo-Wei

AU - Zhong, Guofu

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: We thank the NSFC (21302032 and 21373073) and the PCSIRT (IRT 1231) for financial support. G.Z. appreciates a QjanJiang Scholar from Zhejiang Province in China.

PY - 2014/7/2

Y1 - 2014/7/2

N2 - A facile N-heterocyclic carbene catalytic enantioselective aza-Diels-Alder reaction of oxodiazenes with α-chloroaldehydes as dienophile precursors is reported, with excellent enantioselectivity (ee > 99%) and excellent yield (up to 93%). DFT study showed that cis-TSa, formed from a top face approach of oxodiazene to cis-IIa, is the most favorable transition state and is consistent with the experimental observations. © 2014 American Chemical Society.

AB - A facile N-heterocyclic carbene catalytic enantioselective aza-Diels-Alder reaction of oxodiazenes with α-chloroaldehydes as dienophile precursors is reported, with excellent enantioselectivity (ee > 99%) and excellent yield (up to 93%). DFT study showed that cis-TSa, formed from a top face approach of oxodiazene to cis-IIa, is the most favorable transition state and is consistent with the experimental observations. © 2014 American Chemical Society.

UR - http://hdl.handle.net/10754/563681

UR - https://pubs.acs.org/doi/10.1021/ol501424f

UR - http://www.scopus.com/inward/record.url?scp=84905372043&partnerID=8YFLogxK

U2 - 10.1021/ol501424f

DO - 10.1021/ol501424f

M3 - Article

C2 - 24987938

SN - 1523-7060

VL - 16

SP - 3872

EP - 3875

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Asymmetric NHC-catalyzed aza-Diels-Alder reactions: Highly enantioselective route to α-amino acid derivatives and DFT calculations

Abstract

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CCDC 881370: Experimental Crystal Structure Determination : 5-(4-bromobenzyl)-2-(2-naphthyl)-4-phenyl-4,5-dihydro-6H-1,3,4-oxadiazin-6-one

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Asymmetric NHC-catalyzed aza-Diels-Alder reactions: Highly enantioselective route to α-amino acid derivatives and DFT calculations

Abstract

ASJC Scopus subject areas

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CCDC 881370: Experimental Crystal Structure Determination : 5-(4-bromobenzyl)-2-(2-naphthyl)-4-phenyl-4,5-dihydro-6H-1,3,4-oxadiazin-6-one

Cite this