Efficient syntheses and ring-opening reactions of trans- and cis-Oxazoline-5-carboxylates

Sang Hyeup Lee; Juyoung Yoon; Kensuke Nakamura; Yoon Sik Lee

doi:10.1021/ol005681h

Efficient syntheses and ring-opening reactions of trans- and cis-Oxazoline-5-carboxylates

Sang Hyeup Lee, Juyoung Yoon, Kensuke Nakamura, Yoon Sik Lee

Department of Chemistry & Nanoscience

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

39 Scopus citations

Abstract

cis- and trans-Oxazoline-5-carboxylates were synthesized effeciently from isopropyl trans-cinnamate utilizing the sharpless AA reaction. trans-Oxazoline was much more reactive than the cis-isomer toward ring opening reactions. From ab initio molecular calculation, the cis-isomer was predicted to be less reactive than the trans-isomer by 2.7 kcal/mol. Both syn and anti acetylthio ester and anti diamino ester were synthesized from these cis- and trans- oxazoline-5-carboxylates.

Original language	English
Pages (from-to)	1243-1246
Number of pages	4
Journal	Organic Letters
Volume	2
Issue number	9
DOIs	https://doi.org/10.1021/ol005681h
State	Published - 4 May 2000

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title = "Efficient syntheses and ring-opening reactions of trans- and cis-Oxazoline-5-carboxylates",

abstract = "cis- and trans-Oxazoline-5-carboxylates were synthesized effeciently from isopropyl trans-cinnamate utilizing the sharpless AA reaction. trans-Oxazoline was much more reactive than the cis-isomer toward ring opening reactions. From ab initio molecular calculation, the cis-isomer was predicted to be less reactive than the trans-isomer by 2.7 kcal/mol. Both syn and anti acetylthio ester and anti diamino ester were synthesized from these cis- and trans- oxazoline-5-carboxylates.",

author = "Lee, {Sang Hyeup} and Juyoung Yoon and Kensuke Nakamura and Lee, {Yoon Sik}",

year = "2000",

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doi = "10.1021/ol005681h",

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journal = "Organic Letters",

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T1 - Efficient syntheses and ring-opening reactions of trans- and cis-Oxazoline-5-carboxylates

AU - Lee, Sang Hyeup

AU - Yoon, Juyoung

AU - Nakamura, Kensuke

AU - Lee, Yoon Sik

PY - 2000/5/4

Y1 - 2000/5/4

N2 - cis- and trans-Oxazoline-5-carboxylates were synthesized effeciently from isopropyl trans-cinnamate utilizing the sharpless AA reaction. trans-Oxazoline was much more reactive than the cis-isomer toward ring opening reactions. From ab initio molecular calculation, the cis-isomer was predicted to be less reactive than the trans-isomer by 2.7 kcal/mol. Both syn and anti acetylthio ester and anti diamino ester were synthesized from these cis- and trans- oxazoline-5-carboxylates.

AB - cis- and trans-Oxazoline-5-carboxylates were synthesized effeciently from isopropyl trans-cinnamate utilizing the sharpless AA reaction. trans-Oxazoline was much more reactive than the cis-isomer toward ring opening reactions. From ab initio molecular calculation, the cis-isomer was predicted to be less reactive than the trans-isomer by 2.7 kcal/mol. Both syn and anti acetylthio ester and anti diamino ester were synthesized from these cis- and trans- oxazoline-5-carboxylates.

UR - http://www.scopus.com/inward/record.url?scp=0001612841&partnerID=8YFLogxK

U2 - 10.1021/ol005681h

DO - 10.1021/ol005681h

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SP - 1243

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JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

Efficient syntheses and ring-opening reactions of trans- and cis-Oxazoline-5-carboxylates

Abstract

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