Chiral Lewis Acid-Catalyzed Asymmetric Multicomponent Michael Reaction through [1,2]-Phospha-Brook Rearrangement
The multicomponent catalytic asymmetric Pudovik addition/[1,2]-phospha-Brook rearrangement/Michael reaction sequence of isatins, phosphites, and 4-oxobutenoates was realized. A series of oxindole derivatives containing two contiguous stereocenters was obtained in high yields and excellent stereosele...
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| Published in | Organic letters Vol. 25; no. 34; pp. 6262 - 6266 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
01.09.2023
Amer Chemical Soc |
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| Abstract | The multicomponent catalytic asymmetric Pudovik addition/[1,2]-phospha-Brook rearrangement/Michael reaction sequence of isatins, phosphites, and 4-oxobutenoates was realized. A series of oxindole derivatives containing two contiguous stereocenters was obtained in high yields and excellent stereoselectivities (up to >99% yield, >95:5 dr, >99% ee) using a chiral Lewis acid catalyst. A possible catalytic model is presented to illustrate the stereocontrol. |
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| AbstractList | The multicomponent catalytic asymmetric Pudovik addition/[1,2]-phospha-Brook rearrangement/Michael reaction sequence of isatins, phosphites, and 4-oxobutenoates was realized. A series of oxindole derivatives containing two contiguous stereocenters was obtained in high yields and excellent stereoselectivities (up to >99% yield, >95:5 dr, >99% ee) using a chiral Lewis acid catalyst. A possible catalytic model is presented to illustrate the stereocontrol. The multicomponent catalytic asymmetric Pudovik addition/[1,2]-phospha-Brookrearrangement/Michael reaction sequence of isatins, phosphites, and4-oxobutenoates was realized. A series of oxindole derivatives containingtwo contiguous stereocenters was obtained in high yields and excellentstereoselectivities (up to >99% yield, >95:5 dr, >99% ee)using achiral Lewis acid catalyst. A possible catalytic model is presentedto illustrate the stereocontrol. |
| Author | Feng, Xiaoming Lin, Qianchi Cao, Weidi Wang, Siyuan Weng, Rui |
| AuthorAffiliation | Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry |
| AuthorAffiliation_xml | – name: Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry |
| Author_xml | – sequence: 1 givenname: Qianchi surname: Lin fullname: Lin, Qianchi – sequence: 2 givenname: Siyuan surname: Wang fullname: Wang, Siyuan – sequence: 3 givenname: Rui surname: Weng fullname: Weng, Rui – sequence: 4 givenname: Weidi orcidid: 0000-0003-1440-4682 surname: Cao fullname: Cao, Weidi email: wdcao@scu.edu.cn – sequence: 5 givenname: Xiaoming orcidid: 0000-0003-4507-0478 surname: Feng fullname: Feng, Xiaoming email: xmfeng@scu.edu.cn |
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| CitedBy_id | crossref_primary_10_1021_acs_joc_4c01570 crossref_primary_10_6023_A23110487 crossref_primary_10_1039_D4DT00061G crossref_primary_10_1002_adsc_202301503 crossref_primary_10_1002_chem_202402967 crossref_primary_10_1016_j_ymeth_2023_11_001 crossref_primary_10_1021_acssuschemeng_4c05293 crossref_primary_10_1016_j_molstruc_2025_141768 crossref_primary_10_1002_cctc_202401324 crossref_primary_10_1021_acscatal_4c04078 |
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| Keywords | CHEMISTRY CYCLOADDITION ALPHA-KETOESTERS LIGANDS ISATINS |
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| Snippet | The multicomponent catalytic asymmetric Pudovik addition/[1,2]-phospha-Brook rearrangement/Michael reaction sequence of isatins, phosphites, and... The multicomponent catalytic asymmetric Pudovik addition/[1,2]-phospha-Brookrearrangement/Michael reaction sequence of isatins, phosphites, and4-oxobutenoates... |
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| SubjectTerms | catalysts chemical reactions Chemistry Chemistry, Organic Lewis acids Physical Sciences Science & Technology |
| Title | Chiral Lewis Acid-Catalyzed Asymmetric Multicomponent Michael Reaction through [1,2]-Phospha-Brook Rearrangement |
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