Catalytic Enantioselective Synthesis of 2,3-Dihydrobenzo[b]oxepines via Asymmetric Oxetane Opening by Internal Carbon Nucleophiles

Tianyu Zhang; Han Zhuang; Luning Tang; Zhengyu Han; Wengang Guo; Hai Huang; Jianwei Sun

doi:10.1021/acs.orglett.1c03852

Catalytic Enantioselective Synthesis of 2,3-Dihydrobenzo[b]oxepines via Asymmetric Oxetane Opening by Internal Carbon Nucleophiles

Tianyu Zhang
, Han Zhuang
, Luning Tang
, Zhengyu Han
, Wengang Guo
, Hai Huang^*
, Jianwei Sun^*

^*Corresponding author for this work

Department of Chemistry

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

20 Citations (Scopus)

Abstract

An intramolecular C–C formation process based on catalytic asymmetric oxetane opening by carbon nucleophiles has been developed, which provides rapid access to a range of valuable enantioenriched 2,3-dihydrobenzo[b]oxepines. With the combination of Sc(OTf)₃ and a Box ligand, good chemical efficiency and enantioselectivity were achieved under mild conditions. The products are also useful precursors to other valuable structures, such as the bicyclo[3.2.2]nonane derivatives.

Original language	English
Pages (from-to)	207-212
Number of pages	6
Journal	Organic Letters
Volume	24
Issue number	1
DOIs	https://doi.org/10.1021/acs.orglett.1c03852
Publication status	Published - 14 Jan 2022

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© 2021 American Chemical Society

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title = "Catalytic Enantioselective Synthesis of 2,3-Dihydrobenzo[b]oxepines via Asymmetric Oxetane Opening by Internal Carbon Nucleophiles",

abstract = "An intramolecular C–C formation process based on catalytic asymmetric oxetane opening by carbon nucleophiles has been developed, which provides rapid access to a range of valuable enantioenriched 2,3-dihydrobenzo[b]oxepines. With the combination of Sc(OTf)3 and a Box ligand, good chemical efficiency and enantioselectivity were achieved under mild conditions. The products are also useful precursors to other valuable structures, such as the bicyclo[3.2.2]nonane derivatives.",

author = "Tianyu Zhang and Han Zhuang and Luning Tang and Zhengyu Han and Wengang Guo and Hai Huang and Jianwei Sun",

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doi = "10.1021/acs.orglett.1c03852",

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T1 - Catalytic Enantioselective Synthesis of 2,3-Dihydrobenzo[b]oxepines via Asymmetric Oxetane Opening by Internal Carbon Nucleophiles

AU - Zhang, Tianyu

AU - Zhuang, Han

AU - Tang, Luning

AU - Han, Zhengyu

AU - Guo, Wengang

AU - Huang, Hai

AU - Sun, Jianwei

PY - 2022/1/14

Y1 - 2022/1/14

N2 - An intramolecular C–C formation process based on catalytic asymmetric oxetane opening by carbon nucleophiles has been developed, which provides rapid access to a range of valuable enantioenriched 2,3-dihydrobenzo[b]oxepines. With the combination of Sc(OTf)3 and a Box ligand, good chemical efficiency and enantioselectivity were achieved under mild conditions. The products are also useful precursors to other valuable structures, such as the bicyclo[3.2.2]nonane derivatives.

AB - An intramolecular C–C formation process based on catalytic asymmetric oxetane opening by carbon nucleophiles has been developed, which provides rapid access to a range of valuable enantioenriched 2,3-dihydrobenzo[b]oxepines. With the combination of Sc(OTf)3 and a Box ligand, good chemical efficiency and enantioselectivity were achieved under mild conditions. The products are also useful precursors to other valuable structures, such as the bicyclo[3.2.2]nonane derivatives.

UR - https://www.webofscience.com/wos/woscc/full-record/WOS:000733803500001

UR - https://openalex.org/W4200589816

U2 - 10.1021/acs.orglett.1c03852

DO - 10.1021/acs.orglett.1c03852

M3 - Journal Article

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SN - 1523-7060

VL - 24

SP - 207

EP - 212

JO - Organic Letters

JF - Organic Letters

IS - 1

ER -

Catalytic Enantioselective Synthesis of 2,3-Dihydrobenzo[b]oxepines via Asymmetric Oxetane Opening by Internal Carbon Nucleophiles

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