Lewis acid mediated diastereoselective allylation of camphorpyrazolidinone derived α-ketoamides

Shy Guey Wang; Huei Ru Tsai; Kwunmin Chen

doi:10.1016/j.tetlet.2004.05.146

Lewis acid mediated diastereoselective allylation of camphorpyrazolidinone derived α-ketoamides

Shy Guey Wang
, Huei Ru Tsai
, Kwunmin Chen^*

^*Corresponding author for this work

Department of Chemistry

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

13 Citations (Scopus)

Abstract

Diastereoselective allylation of camphorpyrazolidinone derived α-ketoamides was examined using allyltributyltin in the presence of various Lewis acids. The corresponding optically enriched quarternary α-hydroxy carbonyls were obtained in reasonable to excellent material yields (51-95%) and with practical levels of stereoselectivity (up to >95% de) when a stoichiometric amount of Sn(OTf)₂ was used. The stereochemical induction is discussed.

Original language	English
Pages (from-to)	6183-6185
Number of pages	3
Journal	Tetrahedron Letters
Volume	45
Issue number	32
DOIs	https://doi.org/10.1016/j.tetlet.2004.05.146
Publication status	Published - 2004 Aug 2

Keywords

Allylation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2004.05.146

Cite this

@article{d89e47128c2642f18ed87218f2721712,

title = "Lewis acid mediated diastereoselective allylation of camphorpyrazolidinone derived α-ketoamides",

abstract = "Diastereoselective allylation of camphorpyrazolidinone derived α-ketoamides was examined using allyltributyltin in the presence of various Lewis acids. The corresponding optically enriched quarternary α-hydroxy carbonyls were obtained in reasonable to excellent material yields (51-95\%) and with practical levels of stereoselectivity (up to >95\% de) when a stoichiometric amount of Sn(OTf)2 was used. The stereochemical induction is discussed.",

keywords = "Allylation",

author = "Wang, \{Shy Guey\} and Tsai, \{Huei Ru\} and Kwunmin Chen",

note = "Funding Information: This work was supported by the National Science Council of the Republic of China (NSC 92-2113-M-003-017 and NSC 92-2751-B-001-014-Y) and the National Taiwan Normal University (ORD 91-2). The X-ray crystal data were collected and processed by Taipei Instrumentation Center, College of Science, National Taiwan University and National Taiwan Normal University are gratefully acknowledged.",

year = "2004",

month = aug,

day = "2",

doi = "10.1016/j.tetlet.2004.05.146",

language = "English",

volume = "45",

pages = "6183--6185",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "32",

}

TY - JOUR

T1 - Lewis acid mediated diastereoselective allylation of camphorpyrazolidinone derived α-ketoamides

AU - Wang, Shy Guey

AU - Tsai, Huei Ru

AU - Chen, Kwunmin

N1 - Funding Information: This work was supported by the National Science Council of the Republic of China (NSC 92-2113-M-003-017 and NSC 92-2751-B-001-014-Y) and the National Taiwan Normal University (ORD 91-2). The X-ray crystal data were collected and processed by Taipei Instrumentation Center, College of Science, National Taiwan University and National Taiwan Normal University are gratefully acknowledged.

PY - 2004/8/2

Y1 - 2004/8/2

N2 - Diastereoselective allylation of camphorpyrazolidinone derived α-ketoamides was examined using allyltributyltin in the presence of various Lewis acids. The corresponding optically enriched quarternary α-hydroxy carbonyls were obtained in reasonable to excellent material yields (51-95%) and with practical levels of stereoselectivity (up to >95% de) when a stoichiometric amount of Sn(OTf)2 was used. The stereochemical induction is discussed.

AB - Diastereoselective allylation of camphorpyrazolidinone derived α-ketoamides was examined using allyltributyltin in the presence of various Lewis acids. The corresponding optically enriched quarternary α-hydroxy carbonyls were obtained in reasonable to excellent material yields (51-95%) and with practical levels of stereoselectivity (up to >95% de) when a stoichiometric amount of Sn(OTf)2 was used. The stereochemical induction is discussed.

KW - Allylation

UR - https://www.scopus.com/pages/publications/3142683546

UR - https://www.scopus.com/pages/publications/3142683546#tab=citedBy

U2 - 10.1016/j.tetlet.2004.05.146

DO - 10.1016/j.tetlet.2004.05.146

M3 - Article

AN - SCOPUS:3142683546

SN - 0040-4039

VL - 45

SP - 6183

EP - 6185

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 32

ER -

Lewis acid mediated diastereoselective allylation of camphorpyrazolidinone derived α-ketoamides

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

CCDC 247167: Experimental Crystal Structure Determination

CCDC 247166: Experimental Crystal Structure Determination

Cite this

Lewis acid mediated diastereoselective allylation of camphorpyrazolidinone derived α-ketoamides

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 247167: Experimental Crystal Structure Determination

CCDC 247166: Experimental Crystal Structure Determination

Cite this