Asymmetric catalytic [4+3] cycloaddition ofortho-quinone methides with oxiranes

Qingfa Tan; Han Yu; Yao Luo; Fenzhen Chang; Xiaohua Liu; Yuqiao Zhou; Xiaoming Feng

doi:10.1039/d1cc00262g

Asymmetric catalytic [4+3] cycloaddition ofortho-quinone methides with oxiranes

Qingfa Tan, Han Yu, Yao Luo, Fenzhen Chang, Xiaohua Liu, Yuqiao Zhou, Xiaoming Feng

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

24 Scopus citations

Abstract

Catalytic enantioselective [4+3] cycloaddition reaction betweeno-quinone methides and oxiranes was achieved by using a chiralN,N′-dioxide/TbIIIcomplex as the catalyst, affording medium-sized hydrodioxepine derivatives in high yields (up to 99%) with good to excellent diastereo-(up to 94 : 6 dr) and enantioselectivities (up to 97% ee). The topographic steric maps and distribution of the buried volume (%VBur) of the catalystsviaCavallo's SambVca 2 tool were collected to effectively represent the chiral pocket of metal complexes of chiralN,N′-dioxides.

Original language	English (US)
Pages (from-to)	3018-3021
Number of pages	4
Journal	Chemical Communications
Volume	57
Issue number	24
DOIs	https://doi.org/10.1039/d1cc00262g
State	Published - Feb 24 2021
Externally published	Yes

Bibliographical note

KAUST Repository Item: Exported on 2022-06-15
Acknowledgements: We appreciate the National Natural Science Foundation of China (21890723, and 21625205) for financial support. The authors give thanks to Dr Luigi Cavallo (KAUST) and Dr Emanuel Hupf (Freie Universität Berlin) for the help in the application of the SambVca 2 suite.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.

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title = "Asymmetric catalytic [4+3] cycloaddition ofortho-quinone methides with oxiranes",

abstract = "Catalytic enantioselective [4+3] cycloaddition reaction betweeno-quinone methides and oxiranes was achieved by using a chiralN,N′-dioxide/TbIIIcomplex as the catalyst, affording medium-sized hydrodioxepine derivatives in high yields (up to 99%) with good to excellent diastereo-(up to 94 : 6 dr) and enantioselectivities (up to 97% ee). The topographic steric maps and distribution of the buried volume (%VBur) of the catalystsviaCavallo's SambVca 2 tool were collected to effectively represent the chiral pocket of metal complexes of chiralN,N′-dioxides.",

author = "Qingfa Tan and Han Yu and Yao Luo and Fenzhen Chang and Xiaohua Liu and Yuqiao Zhou and Xiaoming Feng",

note = "KAUST Repository Item: Exported on 2022-06-15 Acknowledgements: We appreciate the National Natural Science Foundation of China (21890723, and 21625205) for financial support. The authors give thanks to Dr Luigi Cavallo (KAUST) and Dr Emanuel Hupf (Freie Universit{\"a}t Berlin) for the help in the application of the SambVca 2 suite. This publication acknowledges KAUST support, but has no KAUST affiliated authors.",

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doi = "10.1039/d1cc00262g",

language = "English (US)",

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T1 - Asymmetric catalytic [4+3] cycloaddition ofortho-quinone methides with oxiranes

AU - Tan, Qingfa

AU - Yu, Han

AU - Luo, Yao

AU - Chang, Fenzhen

AU - Liu, Xiaohua

AU - Zhou, Yuqiao

AU - Feng, Xiaoming

N1 - KAUST Repository Item: Exported on 2022-06-15 Acknowledgements: We appreciate the National Natural Science Foundation of China (21890723, and 21625205) for financial support. The authors give thanks to Dr Luigi Cavallo (KAUST) and Dr Emanuel Hupf (Freie Universität Berlin) for the help in the application of the SambVca 2 suite. This publication acknowledges KAUST support, but has no KAUST affiliated authors.

PY - 2021/2/24

Y1 - 2021/2/24

N2 - Catalytic enantioselective [4+3] cycloaddition reaction betweeno-quinone methides and oxiranes was achieved by using a chiralN,N′-dioxide/TbIIIcomplex as the catalyst, affording medium-sized hydrodioxepine derivatives in high yields (up to 99%) with good to excellent diastereo-(up to 94 : 6 dr) and enantioselectivities (up to 97% ee). The topographic steric maps and distribution of the buried volume (%VBur) of the catalystsviaCavallo's SambVca 2 tool were collected to effectively represent the chiral pocket of metal complexes of chiralN,N′-dioxides.

AB - Catalytic enantioselective [4+3] cycloaddition reaction betweeno-quinone methides and oxiranes was achieved by using a chiralN,N′-dioxide/TbIIIcomplex as the catalyst, affording medium-sized hydrodioxepine derivatives in high yields (up to 99%) with good to excellent diastereo-(up to 94 : 6 dr) and enantioselectivities (up to 97% ee). The topographic steric maps and distribution of the buried volume (%VBur) of the catalystsviaCavallo's SambVca 2 tool were collected to effectively represent the chiral pocket of metal complexes of chiralN,N′-dioxides.

UR - http://hdl.handle.net/10754/679035

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U2 - 10.1039/d1cc00262g

DO - 10.1039/d1cc00262g

M3 - Article

C2 - 33624677

SN - 1364-548X

VL - 57

SP - 3018

EP - 3021

JO - Chemical Communications

JF - Chemical Communications

IS - 24

ER -

Asymmetric catalytic [4+3] cycloaddition ofortho-quinone methides with oxiranes

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