An efficient diastereoselective glyoxylate-ene reaction using N-glyoxyloyl camphorpyrazolidinone as an enophile

Jia Fu Pan; Uppala Venkatesham; Kwunmin Chen

doi:10.1016/j.tetlet.2004.10.121

An efficient diastereoselective glyoxylate-ene reaction using N-glyoxyloyl camphorpyrazolidinone as an enophile

Jia Fu Pan, Uppala Venkatesham, Kwunmin Chen

Department of Chemistry

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

8 Citations (Scopus)

Abstract

The diastereoselective glyoxylate-ene reaction of N-glyoxyloyl camphorpyrazolidinone (1) with various alkenes 2a-g in the presence of Lewis acid is described. The corresponding α-hydroxyl carbonyls were generally obtained in moderate to high chemical yields (64-87%) and with high levels of diastereoselectivities (up to 94% de). The predominance of products with the S absolute configuration at the newly formed stereogenic center was established by single crystal X-ray analysis and the importance of stereochemical induction is discussed.

Original language	English
Pages (from-to)	9345-9347
Number of pages	3
Journal	Tetrahedron Letters
Volume	45
Issue number	51
DOIs	https://doi.org/10.1016/j.tetlet.2004.10.121
Publication status	Published - 2004 Dec 13

Keywords

Diastereoselective
Glyoxylate-ene reaction
Stereogenic center

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "An efficient diastereoselective glyoxylate-ene reaction using N-glyoxyloyl camphorpyrazolidinone as an enophile",

abstract = "The diastereoselective glyoxylate-ene reaction of N-glyoxyloyl camphorpyrazolidinone (1) with various alkenes 2a-g in the presence of Lewis acid is described. The corresponding α-hydroxyl carbonyls were generally obtained in moderate to high chemical yields (64-87%) and with high levels of diastereoselectivities (up to 94% de). The predominance of products with the S absolute configuration at the newly formed stereogenic center was established by single crystal X-ray analysis and the importance of stereochemical induction is discussed.",

keywords = "Diastereoselective, Glyoxylate-ene reaction, Stereogenic center",

author = "Pan, {Jia Fu} and Uppala Venkatesham and Kwunmin Chen",

note = "Funding Information: This work was supported by the National Science Council of the Republic of China and the National Taiwan Normal University (NSC 92-2113-M-003-017 and ORD 93-C). 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. Our gratitude also goes to the Academic Paper Editing Clinic, NTNU. ",

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doi = "10.1016/j.tetlet.2004.10.121",

language = "English",

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T1 - An efficient diastereoselective glyoxylate-ene reaction using N-glyoxyloyl camphorpyrazolidinone as an enophile

AU - Pan, Jia Fu

AU - Venkatesham, Uppala

AU - Chen, Kwunmin

N1 - Funding Information: This work was supported by the National Science Council of the Republic of China and the National Taiwan Normal University (NSC 92-2113-M-003-017 and ORD 93-C). 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. Our gratitude also goes to the Academic Paper Editing Clinic, NTNU.

PY - 2004/12/13

Y1 - 2004/12/13

N2 - The diastereoselective glyoxylate-ene reaction of N-glyoxyloyl camphorpyrazolidinone (1) with various alkenes 2a-g in the presence of Lewis acid is described. The corresponding α-hydroxyl carbonyls were generally obtained in moderate to high chemical yields (64-87%) and with high levels of diastereoselectivities (up to 94% de). The predominance of products with the S absolute configuration at the newly formed stereogenic center was established by single crystal X-ray analysis and the importance of stereochemical induction is discussed.

AB - The diastereoselective glyoxylate-ene reaction of N-glyoxyloyl camphorpyrazolidinone (1) with various alkenes 2a-g in the presence of Lewis acid is described. The corresponding α-hydroxyl carbonyls were generally obtained in moderate to high chemical yields (64-87%) and with high levels of diastereoselectivities (up to 94% de). The predominance of products with the S absolute configuration at the newly formed stereogenic center was established by single crystal X-ray analysis and the importance of stereochemical induction is discussed.

KW - Diastereoselective

KW - Glyoxylate-ene reaction

KW - Stereogenic center

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DO - 10.1016/j.tetlet.2004.10.121

M3 - Article

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EP - 9347

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

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ER -

An efficient diastereoselective glyoxylate-ene reaction using N-glyoxyloyl camphorpyrazolidinone as an enophile

Abstract

Keywords

ASJC Scopus subject areas

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