Tylophorine via Catalytic Asymmetric Allylation and One ... · 1 Det.ACh1 / 254m Detector A Chl...
Transcript of Tylophorine via Catalytic Asymmetric Allylation and One ... · 1 Det.ACh1 / 254m Detector A Chl...
![Page 1: Tylophorine via Catalytic Asymmetric Allylation and One ... · 1 Det.ACh1 / 254m Detector A Chl 254mn Peak# Ret. Time 12.062 15.385 Tota 491391 375272 866663 49.947 50.053 100.000](https://reader034.fdocuments.in/reader034/viewer/2022051823/5fee2cab301f050f2c353c8c/html5/thumbnails/1.jpg)
1
An Enantioselective Strategy for the Total Synthesis of (S)-Tylophorine via Catalytic Asymmetric Allylation and One-Pot DMAP-Promoted Isocyanate Formation/Lewis Acid Catalyzed Cyclization Sequence
Bo Su, Hui Zhang, Meng Deng, and Qingmin Wang*
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People’s Republic of China
[email protected]; [email protected]
Table of contents1. NMR spectra S22. HPLC data S13
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2014
![Page 2: Tylophorine via Catalytic Asymmetric Allylation and One ... · 1 Det.ACh1 / 254m Detector A Chl 254mn Peak# Ret. Time 12.062 15.385 Tota 491391 375272 866663 49.947 50.053 100.000](https://reader034.fdocuments.in/reader034/viewer/2022051823/5fee2cab301f050f2c353c8c/html5/thumbnails/2.jpg)
2
NMR Data
![Page 3: Tylophorine via Catalytic Asymmetric Allylation and One ... · 1 Det.ACh1 / 254m Detector A Chl 254mn Peak# Ret. Time 12.062 15.385 Tota 491391 375272 866663 49.947 50.053 100.000](https://reader034.fdocuments.in/reader034/viewer/2022051823/5fee2cab301f050f2c353c8c/html5/thumbnails/3.jpg)
3
![Page 4: Tylophorine via Catalytic Asymmetric Allylation and One ... · 1 Det.ACh1 / 254m Detector A Chl 254mn Peak# Ret. Time 12.062 15.385 Tota 491391 375272 866663 49.947 50.053 100.000](https://reader034.fdocuments.in/reader034/viewer/2022051823/5fee2cab301f050f2c353c8c/html5/thumbnails/4.jpg)
4
![Page 5: Tylophorine via Catalytic Asymmetric Allylation and One ... · 1 Det.ACh1 / 254m Detector A Chl 254mn Peak# Ret. Time 12.062 15.385 Tota 491391 375272 866663 49.947 50.053 100.000](https://reader034.fdocuments.in/reader034/viewer/2022051823/5fee2cab301f050f2c353c8c/html5/thumbnails/5.jpg)
5
![Page 6: Tylophorine via Catalytic Asymmetric Allylation and One ... · 1 Det.ACh1 / 254m Detector A Chl 254mn Peak# Ret. Time 12.062 15.385 Tota 491391 375272 866663 49.947 50.053 100.000](https://reader034.fdocuments.in/reader034/viewer/2022051823/5fee2cab301f050f2c353c8c/html5/thumbnails/6.jpg)
6
![Page 7: Tylophorine via Catalytic Asymmetric Allylation and One ... · 1 Det.ACh1 / 254m Detector A Chl 254mn Peak# Ret. Time 12.062 15.385 Tota 491391 375272 866663 49.947 50.053 100.000](https://reader034.fdocuments.in/reader034/viewer/2022051823/5fee2cab301f050f2c353c8c/html5/thumbnails/7.jpg)
7
![Page 8: Tylophorine via Catalytic Asymmetric Allylation and One ... · 1 Det.ACh1 / 254m Detector A Chl 254mn Peak# Ret. Time 12.062 15.385 Tota 491391 375272 866663 49.947 50.053 100.000](https://reader034.fdocuments.in/reader034/viewer/2022051823/5fee2cab301f050f2c353c8c/html5/thumbnails/8.jpg)
8
![Page 9: Tylophorine via Catalytic Asymmetric Allylation and One ... · 1 Det.ACh1 / 254m Detector A Chl 254mn Peak# Ret. Time 12.062 15.385 Tota 491391 375272 866663 49.947 50.053 100.000](https://reader034.fdocuments.in/reader034/viewer/2022051823/5fee2cab301f050f2c353c8c/html5/thumbnails/9.jpg)
9
![Page 10: Tylophorine via Catalytic Asymmetric Allylation and One ... · 1 Det.ACh1 / 254m Detector A Chl 254mn Peak# Ret. Time 12.062 15.385 Tota 491391 375272 866663 49.947 50.053 100.000](https://reader034.fdocuments.in/reader034/viewer/2022051823/5fee2cab301f050f2c353c8c/html5/thumbnails/10.jpg)
10
![Page 11: Tylophorine via Catalytic Asymmetric Allylation and One ... · 1 Det.ACh1 / 254m Detector A Chl 254mn Peak# Ret. Time 12.062 15.385 Tota 491391 375272 866663 49.947 50.053 100.000](https://reader034.fdocuments.in/reader034/viewer/2022051823/5fee2cab301f050f2c353c8c/html5/thumbnails/11.jpg)
11
![Page 12: Tylophorine via Catalytic Asymmetric Allylation and One ... · 1 Det.ACh1 / 254m Detector A Chl 254mn Peak# Ret. Time 12.062 15.385 Tota 491391 375272 866663 49.947 50.053 100.000](https://reader034.fdocuments.in/reader034/viewer/2022051823/5fee2cab301f050f2c353c8c/html5/thumbnails/12.jpg)
12
![Page 13: Tylophorine via Catalytic Asymmetric Allylation and One ... · 1 Det.ACh1 / 254m Detector A Chl 254mn Peak# Ret. Time 12.062 15.385 Tota 491391 375272 866663 49.947 50.053 100.000](https://reader034.fdocuments.in/reader034/viewer/2022051823/5fee2cab301f050f2c353c8c/html5/thumbnails/13.jpg)
13
HPLC data
Conditions for racemic and enantiopure compound 3: Phenomenex Lux Cellulose-1 column, i-PrOH:Hexane = 30:70, 1.0 mL/min, 254nm。
HPLC data for recemic compound 3
![Page 14: Tylophorine via Catalytic Asymmetric Allylation and One ... · 1 Det.ACh1 / 254m Detector A Chl 254mn Peak# Ret. Time 12.062 15.385 Tota 491391 375272 866663 49.947 50.053 100.000](https://reader034.fdocuments.in/reader034/viewer/2022051823/5fee2cab301f050f2c353c8c/html5/thumbnails/14.jpg)
14
HPLC data for compound (R)-3
![Page 15: Tylophorine via Catalytic Asymmetric Allylation and One ... · 1 Det.ACh1 / 254m Detector A Chl 254mn Peak# Ret. Time 12.062 15.385 Tota 491391 375272 866663 49.947 50.053 100.000](https://reader034.fdocuments.in/reader034/viewer/2022051823/5fee2cab301f050f2c353c8c/html5/thumbnails/15.jpg)
15
Conditions for racemic and enantiopure tylophorine: Chiral AD-H column i-PrOH:Hexane = 30:70 (0.1% Et3N), 1.0 mL/min, 254nm。
HPLC data for racemic tylophorine
![Page 16: Tylophorine via Catalytic Asymmetric Allylation and One ... · 1 Det.ACh1 / 254m Detector A Chl 254mn Peak# Ret. Time 12.062 15.385 Tota 491391 375272 866663 49.947 50.053 100.000](https://reader034.fdocuments.in/reader034/viewer/2022051823/5fee2cab301f050f2c353c8c/html5/thumbnails/16.jpg)
16
HPLC data for (S)-tylophorine