Chiral Phosphoric Acid Dual-Function Catalysis : Asymmetric Allylation with α-Vinyl Allylboron Reagents
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim..
We report a dual function asymmetric catalysis by a chiral phosphoric acid catalyst that controls both enantioselective addition of an achiral α-vinyl allylboronate to aldehydes and pseudo-axial orientation of the α-vinyl group in the transition state. The reaction produces dienyl homoallylic alcohols with high Z-selectivities and enantioselectivities. Computational studies revealed that minimization of steric interactions between the alkyl groups of the diol on boron and the chiral phosphoric acid catalyst influence the orientation of α-vinyl substituent of the allylboronate reagent to occupy a pseudo-axial position in the transition state.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2020 |
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| Erschienen: |
2020 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:59 |
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| Enthalten in: |
Angewandte Chemie (International ed. in English) - 59(2020), 26 vom: 22. Juni, Seite 10540-10548 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Gao, Shang [VerfasserIn] |
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| Links: |
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| Themen: |
α-vinyl allylboronate |
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| Anmerkungen: |
Date Completed 11.09.2020 Date Revised 11.09.2020 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1002/anie.202000039 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM307619281 |
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| 245 | 1 | 0 | |a Chiral Phosphoric Acid Dual-Function Catalysis |b Asymmetric Allylation with α-Vinyl Allylboron Reagents |
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| 500 | |a Date Revised 11.09.2020 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. | ||
| 520 | |a We report a dual function asymmetric catalysis by a chiral phosphoric acid catalyst that controls both enantioselective addition of an achiral α-vinyl allylboronate to aldehydes and pseudo-axial orientation of the α-vinyl group in the transition state. The reaction produces dienyl homoallylic alcohols with high Z-selectivities and enantioselectivities. Computational studies revealed that minimization of steric interactions between the alkyl groups of the diol on boron and the chiral phosphoric acid catalyst influence the orientation of α-vinyl substituent of the allylboronate reagent to occupy a pseudo-axial position in the transition state | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, U.S. Gov't, Non-P.H.S. | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 4 | |a asymmetric catalysis | |
| 650 | 4 | |a chiral phosphoric acid | |
| 650 | 4 | |a dual-function catalysis | |
| 650 | 4 | |a α-vinyl allylboronate | |
| 700 | 1 | |a Duan, Meng |e verfasserin |4 aut | |
| 700 | 1 | |a Houk, Kendall N |e verfasserin |4 aut | |
| 700 | 1 | |a Chen, Ming |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Angewandte Chemie (International ed. in English) |d 1964 |g 59(2020), 26 vom: 22. Juni, Seite 10540-10548 |w (DE-627)NLM000105422 |x 1521-3773 |7 nnns |
| 773 | 1 | 8 | |g volume:59 |g year:2020 |g number:26 |g day:22 |g month:06 |g pages:10540-10548 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1002/anie.202000039 |3 Volltext |
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