Catalytic asymmetric synthesis of 19,20-dihydroakuammicine

Ken Ohori; Satoshi Shimizu; Takashi Ohshima; Masakatsu Shibasaki

doi:10.1002/(sici)1520-636x(2000)12:5/6<400::aid-chir18>3.0.co;2-h

Catalytic asymmetric synthesis of 19,20-dihydroakuammicine

Ken Ohori, Satoshi Shimizu, Takashi Ohshima, Masakatsu Shibasaki

Research output: Contribution to journal › Article

19 Citations (Scopus)

Abstract

An enantiocontrolled total synthesis of 19,20-dihydroakuammicine using a catalytic asymmetric MiChael addition of dimethyl malonate to cyclohexenone as the key step is described. The above catalytic asymmetric Michael addition proceeds quite efficiently in the presence of a heterobimetalic asymmetric catalyst (ALB-KO-t-Bu-MS 4A, 0.3 mol%), giving the corresponding Michael adduct in 94% yield and 99% ee. (C) 2000 Wiley-Liss, Inc.

Original language	English
Pages (from-to)	400-403
Number of pages	4
Journal	Chirality
Volume	12
Issue number	5-6
DOIs	https://doi.org/10.1002/(sici)1520-636x(2000)12:5/6<400::aid-chir18>3.0.co;2-h
Publication status	Published - Jan 1 2000
Externally published	Yes

All Science Journal Classification (ASJC) codes

Analytical Chemistry
Catalysis
Pharmacology
Drug Discovery
Spectroscopy
Organic Chemistry

Access to Document

10.1002/(sici)1520-636x(2000)12:5/6<400::aid-chir18>3.0.co;2-h

Fingerprint Dive into the research topics of 'Catalytic asymmetric synthesis of 19,20-dihydroakuammicine'. Together they form a unique fingerprint.

Cite this

@article{4610ec22979847cbb1e05919e1bb7c12,

title = "Catalytic asymmetric synthesis of 19,20-dihydroakuammicine",

abstract = "An enantiocontrolled total synthesis of 19,20-dihydroakuammicine using a catalytic asymmetric MiChael addition of dimethyl malonate to cyclohexenone as the key step is described. The above catalytic asymmetric Michael addition proceeds quite efficiently in the presence of a heterobimetalic asymmetric catalyst (ALB-KO-t-Bu-MS 4A, 0.3 mol%), giving the corresponding Michael adduct in 94% yield and 99% ee. (C) 2000 Wiley-Liss, Inc.",

author = "Ken Ohori and Satoshi Shimizu and Takashi Ohshima and Masakatsu Shibasaki",

year = "2000",

month = jan,

day = "1",

doi = "10.1002/(sici)1520-636x(2000)12:5/6<400::aid-chir18>3.0.co;2-h",

language = "English",

volume = "12",

pages = "400--403",

journal = "Chirality",

issn = "0899-0042",

publisher = "Wiley-Liss Inc.",

number = "5-6",

}

TY - JOUR

T1 - Catalytic asymmetric synthesis of 19,20-dihydroakuammicine

AU - Ohori, Ken

AU - Shimizu, Satoshi

AU - Ohshima, Takashi

AU - Shibasaki, Masakatsu

PY - 2000/1/1

Y1 - 2000/1/1

N2 - An enantiocontrolled total synthesis of 19,20-dihydroakuammicine using a catalytic asymmetric MiChael addition of dimethyl malonate to cyclohexenone as the key step is described. The above catalytic asymmetric Michael addition proceeds quite efficiently in the presence of a heterobimetalic asymmetric catalyst (ALB-KO-t-Bu-MS 4A, 0.3 mol%), giving the corresponding Michael adduct in 94% yield and 99% ee. (C) 2000 Wiley-Liss, Inc.

AB - An enantiocontrolled total synthesis of 19,20-dihydroakuammicine using a catalytic asymmetric MiChael addition of dimethyl malonate to cyclohexenone as the key step is described. The above catalytic asymmetric Michael addition proceeds quite efficiently in the presence of a heterobimetalic asymmetric catalyst (ALB-KO-t-Bu-MS 4A, 0.3 mol%), giving the corresponding Michael adduct in 94% yield and 99% ee. (C) 2000 Wiley-Liss, Inc.

UR - http://www.scopus.com/inward/record.url?scp=0034034225&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0034034225&partnerID=8YFLogxK

U2 - 10.1002/(sici)1520-636x(2000)12:5/6<400::aid-chir18>3.0.co;2-h

DO - 10.1002/(sici)1520-636x(2000)12:5/6<400::aid-chir18>3.0.co;2-h

M3 - Article

C2 - 10824160

AN - SCOPUS:0034034225

VL - 12

SP - 400

EP - 403

JO - Chirality

JF - Chirality

SN - 0899-0042

IS - 5-6

ER -