On the scope of diastereoselective allylation of various chiral glyoxylic oxime ethers with allyltributylstannane in the presence of a Lewis acid and triallylaluminum

Neelesh A. Kulkarni; Ching Fa Yao; Kwunmin Chen

doi:10.1016/j.tet.2007.05.091

On the scope of diastereoselective allylation of various chiral glyoxylic oxime ethers with allyltributylstannane in the presence of a Lewis acid and triallylaluminum

Neelesh A. Kulkarni
, Ching Fa Yao
, Kwunmin Chen^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

15 引文斯高帕斯（Scopus）

摘要

The nucleophilic allylation of various chiral auxiliaries derived glyoxylic oxime ethers was studied. The use of allyltributylstannane in the presence of a Lewis acid and triallylaluminum provided the corresponding homoallylic amines in high chemical yields (up to 89%) and excellent stereoselectivities (up to >99%). The stereochemical bias of the allylation is proposed.

原文	英語
頁（從 - 到）	7816-7822
頁數	7
期刊	Tetrahedron
卷	63
發行號	33
DOIs	https://doi.org/10.1016/j.tet.2007.05.091
出版狀態	已發佈 - 2007 8月 13

ASJC Scopus subject areas

生物化學
藥物發現
有機化學

存取文件

10.1016/j.tet.2007.05.091

其它文件與鏈接

Link to publication in Scopus

CCDC 642119: Experimental Crystal Structure Determination
Kulkarni, N. A. (Creator), Yao, C.-F. (Creator) & Chen, K. (Creator), Unknown Publisher, 2007
DOI: 10.5517/ccpk5jx, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccpk5jx&sid=DataCite
資料集: Dataset
CCDC 642121: Experimental Crystal Structure Determination
Kulkarni, N. A. (Creator), Yao, C.-F. (Creator) & Chen, K. (Creator), Unknown Publisher, 2007
DOI: 10.5517/ccpk5lz, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccpk5lz&sid=DataCite
資料集: Dataset
CCDC 642118: Experimental Crystal Structure Determination
Kulkarni, N. A. (Creator), Yao, C.-F. (Creator) & Chen, K. (Creator), Unknown Publisher, 2007
DOI: 10.5517/ccpk5hw, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccpk5hw&sid=DataCite
資料集: Dataset

引用此

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title = "On the scope of diastereoselective allylation of various chiral glyoxylic oxime ethers with allyltributylstannane in the presence of a Lewis acid and triallylaluminum",

abstract = "The nucleophilic allylation of various chiral auxiliaries derived glyoxylic oxime ethers was studied. The use of allyltributylstannane in the presence of a Lewis acid and triallylaluminum provided the corresponding homoallylic amines in high chemical yields (up to 89\%) and excellent stereoselectivities (up to >99\%). The stereochemical bias of the allylation is proposed.",

keywords = "Allylation, Chiral auxiliary, Glyoxylic oxime ether, Triallylaluminum",

author = "Kulkarni, \{Neelesh A.\} and Yao, \{Ching Fa\} and Kwunmin Chen",

note = "Funding Information: We wish to thank the National Science Council of the Republic of China (NSC 95-2113-M-003-003) and the National Taiwan Normal University (ORD 94-G) for financial support for this work. The X-ray crystal data, which were collected and processed by National Taiwan Normal University, are gratefully acknowledged. ",

year = "2007",

month = aug,

day = "13",

doi = "10.1016/j.tet.2007.05.091",

language = "English",

volume = "63",

pages = "7816--7822",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "33",

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TY - JOUR

T1 - On the scope of diastereoselective allylation of various chiral glyoxylic oxime ethers with allyltributylstannane in the presence of a Lewis acid and triallylaluminum

AU - Kulkarni, Neelesh A.

AU - Yao, Ching Fa

AU - Chen, Kwunmin

N1 - Funding Information: We wish to thank the National Science Council of the Republic of China (NSC 95-2113-M-003-003) and the National Taiwan Normal University (ORD 94-G) for financial support for this work. The X-ray crystal data, which were collected and processed by National Taiwan Normal University, are gratefully acknowledged.

PY - 2007/8/13

Y1 - 2007/8/13

N2 - The nucleophilic allylation of various chiral auxiliaries derived glyoxylic oxime ethers was studied. The use of allyltributylstannane in the presence of a Lewis acid and triallylaluminum provided the corresponding homoallylic amines in high chemical yields (up to 89%) and excellent stereoselectivities (up to >99%). The stereochemical bias of the allylation is proposed.

AB - The nucleophilic allylation of various chiral auxiliaries derived glyoxylic oxime ethers was studied. The use of allyltributylstannane in the presence of a Lewis acid and triallylaluminum provided the corresponding homoallylic amines in high chemical yields (up to 89%) and excellent stereoselectivities (up to >99%). The stereochemical bias of the allylation is proposed.

KW - Allylation

KW - Chiral auxiliary

KW - Glyoxylic oxime ether

KW - Triallylaluminum

UR - https://www.scopus.com/pages/publications/34347267212

UR - https://www.scopus.com/pages/publications/34347267212#tab=citedBy

U2 - 10.1016/j.tet.2007.05.091

DO - 10.1016/j.tet.2007.05.091

M3 - Article

AN - SCOPUS:34347267212

SN - 0040-4020

VL - 63

SP - 7816

EP - 7822

JO - Tetrahedron

JF - Tetrahedron

IS - 33

ER -

On the scope of diastereoselective allylation of various chiral glyoxylic oxime ethers with allyltributylstannane in the presence of a Lewis acid and triallylaluminum

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 642119: Experimental Crystal Structure Determination

CCDC 642121: Experimental Crystal Structure Determination

CCDC 642118: Experimental Crystal Structure Determination

引用此