Asymmetric [2,3]-rearrangement of glycine-derived allyl ammonium ylids

Chemistry

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https://doi.org/10.1021/ja043768i
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Asymmetric [2,3]-rearrangement of glycine-derived allyl ammonium ylids. / Workman, James A.; Garrido, Neil P.; Sançon, Julien et al.
In: Journal of the American Chemical Society, Vol. 127, No. 4, 02.02.2005, p. 1066-1067.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Workman, JA, Garrido, NP, Sançon, J, Roberts, E, Wessel, HP & Sweeney, JB 2005, 'Asymmetric [2,3]-rearrangement of glycine-derived allyl ammonium ylids', Journal of the American Chemical Society, vol. 127, no. 4, pp. 1066-1067. https://doi.org/10.1021/ja043768i

APA

Workman, J. A., Garrido, N. P., Sançon, J., Roberts, E., Wessel, H. P., & Sweeney, J. B. (2005). Asymmetric [2,3]-rearrangement of glycine-derived allyl ammonium ylids. Journal of the American Chemical Society, 127(4), 1066-1067. https://doi.org/10.1021/ja043768i

Vancouver

Workman JA, Garrido NP, Sançon J, Roberts E, Wessel HP, Sweeney JB. Asymmetric [2,3]-rearrangement of glycine-derived allyl ammonium ylids. Journal of the American Chemical Society. 2005 Feb 2;127(4):1066-1067. doi: 10.1021/ja043768i

Author

Workman, James A. ; Garrido, Neil P. ; Sançon, Julien et al. / Asymmetric [2,3]-rearrangement of glycine-derived allyl ammonium ylids. In: Journal of the American Chemical Society. 2005 ; Vol. 127, No. 4. pp. 1066-1067.

Bibtex

@article{b7bae900d19744d5886d857c3ac116f2,

title = "Asymmetric [2,3]-rearrangement of glycine-derived allyl ammonium ylids",

abstract = "The first examples of highly enantioselective [2,3]-sigmatropic rearrangements of acyclic allylic ammonium ylids are reported. Thus, a range of N-{2′-[(N′-allyl-N′,N′-dialkyl)ammonium]}acetyl camphor sultams undergo rearrangement at 0 °C in DME solution with high diastereofacial control (up to 99:1 dr) to give allylglycines in generally high yield. The power of the method has been demonstrated in a rapid and efficient synthesis of (R)-allyl glycine.",

author = "Workman, {James A.} and Garrido, {Neil P.} and Julien San{\c c}on and Edward Roberts and Wessel, {Hans Peter} and Sweeney, {J. B.}",

year = "2005",

month = feb,

day = "2",

doi = "10.1021/ja043768i",

language = "English",

volume = "127",

pages = "1066--1067",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "AMER CHEMICAL SOC",

number = "4",

}

RIS

TY - JOUR

T1 - Asymmetric [2,3]-rearrangement of glycine-derived allyl ammonium ylids

AU - Workman, James A.

AU - Garrido, Neil P.

AU - Sançon, Julien

AU - Roberts, Edward

AU - Wessel, Hans Peter

AU - Sweeney, J. B.

PY - 2005/2/2

Y1 - 2005/2/2

N2 - The first examples of highly enantioselective [2,3]-sigmatropic rearrangements of acyclic allylic ammonium ylids are reported. Thus, a range of N-{2′-[(N′-allyl-N′,N′-dialkyl)ammonium]}acetyl camphor sultams undergo rearrangement at 0 °C in DME solution with high diastereofacial control (up to 99:1 dr) to give allylglycines in generally high yield. The power of the method has been demonstrated in a rapid and efficient synthesis of (R)-allyl glycine.

AB - The first examples of highly enantioselective [2,3]-sigmatropic rearrangements of acyclic allylic ammonium ylids are reported. Thus, a range of N-{2′-[(N′-allyl-N′,N′-dialkyl)ammonium]}acetyl camphor sultams undergo rearrangement at 0 °C in DME solution with high diastereofacial control (up to 99:1 dr) to give allylglycines in generally high yield. The power of the method has been demonstrated in a rapid and efficient synthesis of (R)-allyl glycine.

U2 - 10.1021/ja043768i

DO - 10.1021/ja043768i

M3 - Journal article

C2 - 15669822

AN - SCOPUS:13644259133

VL - 127

SP - 1066

EP - 1067

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 4

ER -

Research

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