Enantioselective Rhodium-Catalyzed Allylation of Aliphatic Imines: Synthesis of Chiral C-Aliphatic Homoallylic Amines

Wei Sian Li; Ting Shen Kuo; Meng Chi Hsieh; Ming Kang Tsai; Ping Yu Wu; Hsyueh Liang Wu

doi:10.1021/acs.orglett.0c02069

Enantioselective Rhodium-Catalyzed Allylation of Aliphatic Imines: Synthesis of Chiral C-Aliphatic Homoallylic Amines

Wei Sian Li, Ting Shen Kuo, Meng Chi Hsieh, Ming Kang Tsai, Ping Yu Wu, Hsyueh Liang Wu

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

Abstract

Reported herein is a method for the efficient syntheses of optically active 1-alkyl homoallylic amines in yields up to 95%, 13.5:1 dr, and 98% ee under mild, aqueous reaction conditions, via the Rh-catalyzed asymmetric allylation of aliphatic aldimines. This method provides a streamlined synthetic platform for the preparation of indolizidine and piperidine alkaloids, thus demonstrating its usefulness.

Original language	English
Pages (from-to)	5675-5679
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	14
DOIs	https://doi.org/10.1021/acs.orglett.0c02069
Publication status	Published - 2020 Jul 17

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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@article{9dfe63b684db42ff92f444d292a299b9,

title = "Enantioselective Rhodium-Catalyzed Allylation of Aliphatic Imines: Synthesis of Chiral C-Aliphatic Homoallylic Amines",

abstract = "Reported herein is a method for the efficient syntheses of optically active 1-alkyl homoallylic amines in yields up to 95%, 13.5:1 dr, and 98% ee under mild, aqueous reaction conditions, via the Rh-catalyzed asymmetric allylation of aliphatic aldimines. This method provides a streamlined synthetic platform for the preparation of indolizidine and piperidine alkaloids, thus demonstrating its usefulness.",

author = "Li, {Wei Sian} and Kuo, {Ting Shen} and Hsieh, {Meng Chi} and Tsai, {Ming Kang} and Wu, {Ping Yu} and Wu, {Hsyueh Liang}",

note = "Funding Information: Financial support from the Ministry of Science and Technology of the Republic of China (104-2628-M-003-001-MY3 and 107-2113-M-003-014-MY3) is gratefully acknowledged.",

year = "2020",

month = jul,

day = "17",

doi = "10.1021/acs.orglett.0c02069",

language = "English",

volume = "22",

pages = "5675--5679",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "14",

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TY - JOUR

T1 - Enantioselective Rhodium-Catalyzed Allylation of Aliphatic Imines

T2 - Synthesis of Chiral C-Aliphatic Homoallylic Amines

AU - Li, Wei Sian

AU - Kuo, Ting Shen

AU - Hsieh, Meng Chi

AU - Tsai, Ming Kang

AU - Wu, Ping Yu

AU - Wu, Hsyueh Liang

N1 - Funding Information: Financial support from the Ministry of Science and Technology of the Republic of China (104-2628-M-003-001-MY3 and 107-2113-M-003-014-MY3) is gratefully acknowledged.

PY - 2020/7/17

Y1 - 2020/7/17

N2 - Reported herein is a method for the efficient syntheses of optically active 1-alkyl homoallylic amines in yields up to 95%, 13.5:1 dr, and 98% ee under mild, aqueous reaction conditions, via the Rh-catalyzed asymmetric allylation of aliphatic aldimines. This method provides a streamlined synthetic platform for the preparation of indolizidine and piperidine alkaloids, thus demonstrating its usefulness.

AB - Reported herein is a method for the efficient syntheses of optically active 1-alkyl homoallylic amines in yields up to 95%, 13.5:1 dr, and 98% ee under mild, aqueous reaction conditions, via the Rh-catalyzed asymmetric allylation of aliphatic aldimines. This method provides a streamlined synthetic platform for the preparation of indolizidine and piperidine alkaloids, thus demonstrating its usefulness.

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JF - Organic Letters

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