Catalytic Asymmetric Pictet–Spengler-Type Reaction for the Synthesis of Optically Active Indolo[3,4-cd][1]benzazepines

A new strategy has been introduced to develop a catalytic asymmetric Pictet–Spengler-type reaction by replacing the aldehyde with an imine. A range of 4-(2-aminoaryl)indoles smoothly undergo the chiral phosphoric acid catalyzed asymmetric Pictet–Spengler-type reaction with imines at room temperature...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2011-10, Vol.13 (20), p.5636-5639
Main Authors: Cheng, Dao-Juan, Wu, Hai-Bian, Tian, Shi-Kai
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-a380t-56658a92120e6c10ef5bc1830570c1c2d7cd94bf56531728099679c0633fc44a3
cites cdi_FETCH-LOGICAL-a380t-56658a92120e6c10ef5bc1830570c1c2d7cd94bf56531728099679c0633fc44a3
container_end_page 5639
container_issue 20
container_start_page 5636
container_title Organic letters
container_volume 13
creator Cheng, Dao-Juan
Wu, Hai-Bian
Tian, Shi-Kai
description A new strategy has been introduced to develop a catalytic asymmetric Pictet–Spengler-type reaction by replacing the aldehyde with an imine. A range of 4-(2-aminoaryl)indoles smoothly undergo the chiral phosphoric acid catalyzed asymmetric Pictet–Spengler-type reaction with imines at room temperature to give structurally diverse indolo[3,4-cd][1]benzazepines in good to excellent yields and ee.
doi_str_mv 10.1021/ol202361t
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_898508141</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>898508141</sourcerecordid><originalsourceid>FETCH-LOGICAL-a380t-56658a92120e6c10ef5bc1830570c1c2d7cd94bf56531728099679c0633fc44a3</originalsourceid><addsrcrecordid>eNptkMtKxDAUhoMoOl4WvoBkIyJYzaXpZTkM3kBQvKwGKZn0VDukTU0yYmflO_iGPomRGWfl6v85fHxwfoT2KTmlhNEzoxlhPKF-DQ2oYDxKiWDrq56QLbTt3JQQGi75JtpiNI-ZSMUAfYykl7r3tcJD1zcNeBvqXa08-O_Pr4cO2hcNNnrsO8D3IJWvTYsrY7F_BfzQtyFc7bCp8G0XLFLrHg8D9Q74ui2NNmN-EkeqfB7T5wm0czmHrm7B7aKNSmoHe8vcQU8X54-jq-jm9vJ6NLyJJM-Ij0SSiEzmjDICiaIEKjFRNONEpERRxcpUlXk8qUQiOE1ZRvI8SXNFEs4rFceS76Cjhbez5m0GzhdN7RRoLVswM1dkeSZIRmMayOMFqaxxzkJVdLZupO0LSorfnYvVzoE9WFpnkwbKFfk3bAAOF4BUrpiamW3Dk_-IfgDBIYVN</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>898508141</pqid></control><display><type>article</type><title>Catalytic Asymmetric Pictet–Spengler-Type Reaction for the Synthesis of Optically Active Indolo[3,4-cd][1]benzazepines</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Cheng, Dao-Juan ; Wu, Hai-Bian ; Tian, Shi-Kai</creator><creatorcontrib>Cheng, Dao-Juan ; Wu, Hai-Bian ; Tian, Shi-Kai</creatorcontrib><description>A new strategy has been introduced to develop a catalytic asymmetric Pictet–Spengler-type reaction by replacing the aldehyde with an imine. A range of 4-(2-aminoaryl)indoles smoothly undergo the chiral phosphoric acid catalyzed asymmetric Pictet–Spengler-type reaction with imines at room temperature to give structurally diverse indolo[3,4-cd][1]benzazepines in good to excellent yields and ee.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol202361t</identifier><identifier>PMID: 21942575</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2011-10, Vol.13 (20), p.5636-5639</ispartof><rights>Copyright © 2011 American Chemical Society</rights><rights>2011 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a380t-56658a92120e6c10ef5bc1830570c1c2d7cd94bf56531728099679c0633fc44a3</citedby><cites>FETCH-LOGICAL-a380t-56658a92120e6c10ef5bc1830570c1c2d7cd94bf56531728099679c0633fc44a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21942575$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Cheng, Dao-Juan</creatorcontrib><creatorcontrib>Wu, Hai-Bian</creatorcontrib><creatorcontrib>Tian, Shi-Kai</creatorcontrib><title>Catalytic Asymmetric Pictet–Spengler-Type Reaction for the Synthesis of Optically Active Indolo[3,4-cd][1]benzazepines</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A new strategy has been introduced to develop a catalytic asymmetric Pictet–Spengler-type reaction by replacing the aldehyde with an imine. A range of 4-(2-aminoaryl)indoles smoothly undergo the chiral phosphoric acid catalyzed asymmetric Pictet–Spengler-type reaction with imines at room temperature to give structurally diverse indolo[3,4-cd][1]benzazepines in good to excellent yields and ee.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNptkMtKxDAUhoMoOl4WvoBkIyJYzaXpZTkM3kBQvKwGKZn0VDukTU0yYmflO_iGPomRGWfl6v85fHxwfoT2KTmlhNEzoxlhPKF-DQ2oYDxKiWDrq56QLbTt3JQQGi75JtpiNI-ZSMUAfYykl7r3tcJD1zcNeBvqXa08-O_Pr4cO2hcNNnrsO8D3IJWvTYsrY7F_BfzQtyFc7bCp8G0XLFLrHg8D9Q74ui2NNmN-EkeqfB7T5wm0czmHrm7B7aKNSmoHe8vcQU8X54-jq-jm9vJ6NLyJJM-Ij0SSiEzmjDICiaIEKjFRNONEpERRxcpUlXk8qUQiOE1ZRvI8SXNFEs4rFceS76Cjhbez5m0GzhdN7RRoLVswM1dkeSZIRmMayOMFqaxxzkJVdLZupO0LSorfnYvVzoE9WFpnkwbKFfk3bAAOF4BUrpiamW3Dk_-IfgDBIYVN</recordid><startdate>20111021</startdate><enddate>20111021</enddate><creator>Cheng, Dao-Juan</creator><creator>Wu, Hai-Bian</creator><creator>Tian, Shi-Kai</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20111021</creationdate><title>Catalytic Asymmetric Pictet–Spengler-Type Reaction for the Synthesis of Optically Active Indolo[3,4-cd][1]benzazepines</title><author>Cheng, Dao-Juan ; Wu, Hai-Bian ; Tian, Shi-Kai</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a380t-56658a92120e6c10ef5bc1830570c1c2d7cd94bf56531728099679c0633fc44a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Cheng, Dao-Juan</creatorcontrib><creatorcontrib>Wu, Hai-Bian</creatorcontrib><creatorcontrib>Tian, Shi-Kai</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Cheng, Dao-Juan</au><au>Wu, Hai-Bian</au><au>Tian, Shi-Kai</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Catalytic Asymmetric Pictet–Spengler-Type Reaction for the Synthesis of Optically Active Indolo[3,4-cd][1]benzazepines</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2011-10-21</date><risdate>2011</risdate><volume>13</volume><issue>20</issue><spage>5636</spage><epage>5639</epage><pages>5636-5639</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A new strategy has been introduced to develop a catalytic asymmetric Pictet–Spengler-type reaction by replacing the aldehyde with an imine. A range of 4-(2-aminoaryl)indoles smoothly undergo the chiral phosphoric acid catalyzed asymmetric Pictet–Spengler-type reaction with imines at room temperature to give structurally diverse indolo[3,4-cd][1]benzazepines in good to excellent yields and ee.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>21942575</pmid><doi>10.1021/ol202361t</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2011-10, Vol.13 (20), p.5636-5639
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_898508141
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
title Catalytic Asymmetric Pictet–Spengler-Type Reaction for the Synthesis of Optically Active Indolo[3,4-cd][1]benzazepines
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-06T19%3A05%3A08IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Catalytic%20Asymmetric%20Pictet%E2%80%93Spengler-Type%20Reaction%20for%20the%20Synthesis%20of%20Optically%20Active%20Indolo%5B3,4-cd%5D%5B1%5Dbenzazepines&rft.jtitle=Organic%20letters&rft.au=Cheng,%20Dao-Juan&rft.date=2011-10-21&rft.volume=13&rft.issue=20&rft.spage=5636&rft.epage=5639&rft.pages=5636-5639&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol202361t&rft_dat=%3Cproquest_cross%3E898508141%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a380t-56658a92120e6c10ef5bc1830570c1c2d7cd94bf56531728099679c0633fc44a3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=898508141&rft_id=info:pmid/21942575&rfr_iscdi=true