Syntheses and Crystal Structures of the Cinchona Alkaloid Derivatives Used as Ligands in the Osmium-Catalyzed Asymmetric Dihydroxylation of Olefins

Willi Amberg, Youssef L. Bennani, Raj K. Chadha, Gerard A. Crispino, William D. Davis, Jens Hartung, Kyu-Sung Jeong, Yasukazu Ogino, Tomoyuki Shibata, K. Barry Sharpless

Research output: Contribution to journalArticle

122 Citations (Scopus)

Abstract

Experimental procedures for the preparation of two classes of derivatives of the cinchona alkaloids dihydroquinine and dihydroquinidine are described. Ligands (DHQ)2-PHAL, 1a, and (DHQD)2-PHAL, 2a, are conveniently synthesized in good yield by the reaction of the corresponding alkaloid with 1,4-dichlorophthalazine in the presence of K2CO3 and KOH in refluxing toluene. Derivatives DHQ-PHN, 1b, and DHQD-PHN, 2b, are prepared through an Ullmann-type coupling between the 9-O-alkaloid sodium alkoxide and 9-iodophenanthrene in the presence of CuI and pyridine. Crystal structures for derivatives 2a and 2b are also presented. These four alkaloid derivatives serve as highly enantioselective ligands for the osmium tetraoxide catalyzed asymmetric dihydroxylation (AD) of olefins.

Original languageEnglish
Pages (from-to)844-849
Number of pages6
JournalJournal of Organic Chemistry
Volume58
Issue number4
DOIs
Publication statusPublished - 1993 Jan 1

Fingerprint

Cinchona Alkaloids
Osmium
Alkenes
Crystal structure
Alkaloids
Ligands
Derivatives
Toluene
Sodium

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Amberg, Willi ; Bennani, Youssef L. ; Chadha, Raj K. ; Crispino, Gerard A. ; Davis, William D. ; Hartung, Jens ; Jeong, Kyu-Sung ; Ogino, Yasukazu ; Shibata, Tomoyuki ; Sharpless, K. Barry. / Syntheses and Crystal Structures of the Cinchona Alkaloid Derivatives Used as Ligands in the Osmium-Catalyzed Asymmetric Dihydroxylation of Olefins. In: Journal of Organic Chemistry. 1993 ; Vol. 58, No. 4. pp. 844-849.
@article{03edb9c7e8304640af33e6263d617670,
title = "Syntheses and Crystal Structures of the Cinchona Alkaloid Derivatives Used as Ligands in the Osmium-Catalyzed Asymmetric Dihydroxylation of Olefins",
abstract = "Experimental procedures for the preparation of two classes of derivatives of the cinchona alkaloids dihydroquinine and dihydroquinidine are described. Ligands (DHQ)2-PHAL, 1a, and (DHQD)2-PHAL, 2a, are conveniently synthesized in good yield by the reaction of the corresponding alkaloid with 1,4-dichlorophthalazine in the presence of K2CO3 and KOH in refluxing toluene. Derivatives DHQ-PHN, 1b, and DHQD-PHN, 2b, are prepared through an Ullmann-type coupling between the 9-O-alkaloid sodium alkoxide and 9-iodophenanthrene in the presence of CuI and pyridine. Crystal structures for derivatives 2a and 2b are also presented. These four alkaloid derivatives serve as highly enantioselective ligands for the osmium tetraoxide catalyzed asymmetric dihydroxylation (AD) of olefins.",
author = "Willi Amberg and Bennani, {Youssef L.} and Chadha, {Raj K.} and Crispino, {Gerard A.} and Davis, {William D.} and Jens Hartung and Kyu-Sung Jeong and Yasukazu Ogino and Tomoyuki Shibata and Sharpless, {K. Barry}",
year = "1993",
month = "1",
day = "1",
doi = "10.1021/jo00056a015",
language = "English",
volume = "58",
pages = "844--849",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "4",

}

Amberg, W, Bennani, YL, Chadha, RK, Crispino, GA, Davis, WD, Hartung, J, Jeong, K-S, Ogino, Y, Shibata, T & Sharpless, KB 1993, 'Syntheses and Crystal Structures of the Cinchona Alkaloid Derivatives Used as Ligands in the Osmium-Catalyzed Asymmetric Dihydroxylation of Olefins', Journal of Organic Chemistry, vol. 58, no. 4, pp. 844-849. https://doi.org/10.1021/jo00056a015

Syntheses and Crystal Structures of the Cinchona Alkaloid Derivatives Used as Ligands in the Osmium-Catalyzed Asymmetric Dihydroxylation of Olefins. / Amberg, Willi; Bennani, Youssef L.; Chadha, Raj K.; Crispino, Gerard A.; Davis, William D.; Hartung, Jens; Jeong, Kyu-Sung; Ogino, Yasukazu; Shibata, Tomoyuki; Sharpless, K. Barry.

In: Journal of Organic Chemistry, Vol. 58, No. 4, 01.01.1993, p. 844-849.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Syntheses and Crystal Structures of the Cinchona Alkaloid Derivatives Used as Ligands in the Osmium-Catalyzed Asymmetric Dihydroxylation of Olefins

AU - Amberg, Willi

AU - Bennani, Youssef L.

AU - Chadha, Raj K.

AU - Crispino, Gerard A.

AU - Davis, William D.

AU - Hartung, Jens

AU - Jeong, Kyu-Sung

AU - Ogino, Yasukazu

AU - Shibata, Tomoyuki

AU - Sharpless, K. Barry

PY - 1993/1/1

Y1 - 1993/1/1

N2 - Experimental procedures for the preparation of two classes of derivatives of the cinchona alkaloids dihydroquinine and dihydroquinidine are described. Ligands (DHQ)2-PHAL, 1a, and (DHQD)2-PHAL, 2a, are conveniently synthesized in good yield by the reaction of the corresponding alkaloid with 1,4-dichlorophthalazine in the presence of K2CO3 and KOH in refluxing toluene. Derivatives DHQ-PHN, 1b, and DHQD-PHN, 2b, are prepared through an Ullmann-type coupling between the 9-O-alkaloid sodium alkoxide and 9-iodophenanthrene in the presence of CuI and pyridine. Crystal structures for derivatives 2a and 2b are also presented. These four alkaloid derivatives serve as highly enantioselective ligands for the osmium tetraoxide catalyzed asymmetric dihydroxylation (AD) of olefins.

AB - Experimental procedures for the preparation of two classes of derivatives of the cinchona alkaloids dihydroquinine and dihydroquinidine are described. Ligands (DHQ)2-PHAL, 1a, and (DHQD)2-PHAL, 2a, are conveniently synthesized in good yield by the reaction of the corresponding alkaloid with 1,4-dichlorophthalazine in the presence of K2CO3 and KOH in refluxing toluene. Derivatives DHQ-PHN, 1b, and DHQD-PHN, 2b, are prepared through an Ullmann-type coupling between the 9-O-alkaloid sodium alkoxide and 9-iodophenanthrene in the presence of CuI and pyridine. Crystal structures for derivatives 2a and 2b are also presented. These four alkaloid derivatives serve as highly enantioselective ligands for the osmium tetraoxide catalyzed asymmetric dihydroxylation (AD) of olefins.

UR - http://www.scopus.com/inward/record.url?scp=0027398106&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0027398106&partnerID=8YFLogxK

U2 - 10.1021/jo00056a015

DO - 10.1021/jo00056a015

M3 - Article

VL - 58

SP - 844

EP - 849

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 4

ER -