Direct catalytic asymmetric aldol reaction of thioamides: A concise asymmetric synthesis of (R)-fluoxetine

Mitsutaka Iwata; Ryo Yazaki; Naoya Kumagai; Masakatsu Shibasaki

doi:10.1016/j.tetasy.2010.04.034

Direct catalytic asymmetric aldol reaction of thioamides: A concise asymmetric synthesis of (R)-fluoxetine

Mitsutaka Iwata
, Ryo Yazaki
, Naoya Kumagai
, Masakatsu Shibasaki

研究成果: ジャーナルへの寄稿 › 学術誌 › 査読

34 被引用数 (Scopus)

抄録

A direct catalytic asymmetric aldol reaction of aromatic aldehydes and thioamides is described. A soft Lewis acid/hard Brønsted base cooperative catalyst comprising (R,R)-Ph-BPE/[Cu(CH₃CN)₄]PF ₆/Li(OC₆H₄-p-OMe) promoted the title reaction efficiently, triggered by in situ generation of the active thioamide enolate through a soft-soft interaction of Cu(I) and the thioamide. The aldol product was transformed into (R)-fluoxetine, an antidepressant agent.

本文言語	英語
ページ（範囲）	1688-1694
ページ数	7
ジャーナル	Tetrahedron Asymmetry
巻	21
号	13-14
DOI	https://doi.org/10.1016/j.tetasy.2010.04.034
出版ステータス	出版済み - 2010
外部発表	はい

!!!All Science Journal Classification (ASJC) codes

触媒
物理化学および理論化学
有機化学
無機化学

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10.1016/j.tetasy.2010.04.034

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title = "Direct catalytic asymmetric aldol reaction of thioamides: A concise asymmetric synthesis of (R)-fluoxetine",

abstract = "A direct catalytic asymmetric aldol reaction of aromatic aldehydes and thioamides is described. A soft Lewis acid/hard Br{\o}nsted base cooperative catalyst comprising (R,R)-Ph-BPE/[Cu(CH3CN)4]PF 6/Li(OC6H4-p-OMe) promoted the title reaction efficiently, triggered by in situ generation of the active thioamide enolate through a soft-soft interaction of Cu(I) and the thioamide. The aldol product was transformed into (R)-fluoxetine, an antidepressant agent.",

author = "Mitsutaka Iwata and Ryo Yazaki and Naoya Kumagai and Masakatsu Shibasaki",

year = "2010",

doi = "10.1016/j.tetasy.2010.04.034",

language = "English",

volume = "21",

pages = "1688--1694",

journal = "Tetrahedron Asymmetry",

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TY - JOUR

T1 - Direct catalytic asymmetric aldol reaction of thioamides

T2 - A concise asymmetric synthesis of (R)-fluoxetine

AU - Iwata, Mitsutaka

AU - Yazaki, Ryo

AU - Kumagai, Naoya

AU - Shibasaki, Masakatsu

PY - 2010

Y1 - 2010

N2 - A direct catalytic asymmetric aldol reaction of aromatic aldehydes and thioamides is described. A soft Lewis acid/hard Brønsted base cooperative catalyst comprising (R,R)-Ph-BPE/[Cu(CH3CN)4]PF 6/Li(OC6H4-p-OMe) promoted the title reaction efficiently, triggered by in situ generation of the active thioamide enolate through a soft-soft interaction of Cu(I) and the thioamide. The aldol product was transformed into (R)-fluoxetine, an antidepressant agent.

AB - A direct catalytic asymmetric aldol reaction of aromatic aldehydes and thioamides is described. A soft Lewis acid/hard Brønsted base cooperative catalyst comprising (R,R)-Ph-BPE/[Cu(CH3CN)4]PF 6/Li(OC6H4-p-OMe) promoted the title reaction efficiently, triggered by in situ generation of the active thioamide enolate through a soft-soft interaction of Cu(I) and the thioamide. The aldol product was transformed into (R)-fluoxetine, an antidepressant agent.

UR - https://www.scopus.com/pages/publications/77956263440

UR - https://www.scopus.com/pages/publications/77956263440#tab=citedBy

U2 - 10.1016/j.tetasy.2010.04.034

DO - 10.1016/j.tetasy.2010.04.034

M3 - Article

AN - SCOPUS:77956263440

SN - 0957-4166

VL - 21

SP - 1688

EP - 1694

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 13-14

ER -

Direct catalytic asymmetric aldol reaction of thioamides: A concise asymmetric synthesis of (R)-fluoxetine

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!!!All Science Journal Classification (ASJC) codes

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