efficient resolution with BINOL, and assignment of absolute configuration by Mosher’s method.pdf
- 1、本文档共7页,可阅读全部内容。
- 2、原创力文档(book118)网站文档一经付费(服务费),不意味着购买了该文档的版权,仅供个人/单位学习、研究之用,不得用于商业用途,未经授权,严禁复制、发行、汇编、翻译或者网络传播等,侵权必究。
- 3、本站所有内容均由合作方或网友上传,本站不对文档的完整性、权威性及其观点立场正确性做任何保证或承诺!文档内容仅供研究参考,付费前请自行鉴别。如您付费,意味着您自己接受本站规则且自行承担风险,本站不退款、不进行额外附加服务;查看《如何避免下载的几个坑》。如果您已付费下载过本站文档,您可以点击 这里二次下载。
- 4、如文档侵犯商业秘密、侵犯著作权、侵犯人身权等,请点击“版权申诉”(推荐),也可以打举报电话:400-050-0827(电话支持时间:9:00-18:30)。
查看更多
efficient resolution with BINOL, and assignment of absolute configuration by Mosher’s method
Tetrahedron: Asymmetry 16 (2005) 2141–2147
Tetrahedron:
AsymmetryThe natural alkaloid isoanabasine: synthesis from
2,3 0-bipyridine, efficient resolution with BINOL, and assignment
of absolute configuration by Moshers method
Chuan-Qing Kang, Yan-Qin Cheng, Hai-Quan Guo, Xue-Peng Qiu and Lian-Xun Gao*
The State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry,
Chinese Academy of Sciences, Graduate School of Chinese Academy of Sciences, 5625 Renmin Street, Changchun 130022, PR China
Received 18 April 2005; accepted 10 May 2005Abstract—A highly efficient and practical resolution of racemic 1-benzylisoanabasine, which was synthesized by reduction of the
benzyl salt of 2,3 0-bipyridine, has been achieved through molecular complexation with (R)-BINOL or (S)-BINOL to afford pure
enantiomers (100% ee). The two enantiomers of the natural alkaloid isoanabasine have been obtained by debenzylation of the cor-
responding enantiomeric 1-benzylisoanabasine. Using Moshers method by NMR techniques, the absolute configuration of ()-iso-
anabasine has been assigned as the (R)-configuration for the first time. Moreover, an unexpected rotamer ratio of Moshers amide
was observed. The syn-form of two rotamers of (R)-MTPA-(R)-isoanabasine was predominant over the anti-form.
2005 Elsevier Ltd. All rights reserved.N N
R
1 R = H
2 R = Bn
OH
OH OH
OHRO CO2H
RO CO2H
5 R = H
6 R = p-Toluoyl
(R)-7 (S)-7
Figure 1. Chiral reagents bearing double acidic groups for resolution.1. Introduction
The rarely investigated minor natural alkaloid isoanaba-
sine 1 (Fig. 1) has been discovered only in low quantities
in the desert plant Anabasis aphylla L., which can be
found in the northwest of China and Central Asia.1 Re-
cently, much attention has been paid to the synthesis
and biological activities of its skeleton analogues includ-
ing natural and synthetic alkaloids, such as anabasine,
anatabine, cytisine, and some other pyridyl piperi-
dines.2,3 These analog
您可能关注的文档
- Conversation Errors in Web Service Coordination Run-time Detection and Repair.pdf
- CONVERSATIONAL INTERACTIVITY IN SLOW-MOTION A COMPARISON OF PHONE DIALOGUES AND OPERA SCENE.pdf
- Conversation2.ppt
- conversation_.doc
- Conversation_with_a_Server_Administrator_ver5.ppt
- Copper and cadmium sorption onto kraft and organosolv lignins.pdf
- Copyright 2002 IFAC 15th Triennial World Congress, Barcelona, Spain ROBUST BOUNDARY CONTRO.pdf
- CORC REPORT 2003-09 Tree-width and the Sherali–Adams operator.pdf
- Core-Collapse Supernovae and Neutron Star Kicks.pdf
- Corn Light.doc
- 【精品】人教版小学语文六年级下册期末考卷含参考答案.docx
- 【精品】人教版小学数学五年级下册期中试卷含参考答案.docx
- 【精品】人教版小学数学五年级下册期末试卷含参考答案.docx
- 【精品】北师大版小学英语五年级下册期末试卷含参考答案.docx
- 【精品】北师大版小学科学一年级上册模拟考卷含参考答案.docx
- 【精品】北师大版小学科学一年级下册期末考卷含参考答案.docx
- 【精品】北师大版小学科学三年级下册期末试卷含参考答案.docx
- 【精品】北师大版小学英语六年级上册模拟考卷含参考答案.docx
- 【精品】人教版小学数学五年级下册期末考卷含参考答案.docx
- 【精品】人教版小学数学五年级上册期末考卷含参考答案.docx
文档评论(0)