Synthesis of chiral tripeptides by asymmetric hydrogenation of dehydrotripeptides. Remarkable effects of N-protecting groups on stereoselectivity and reactivity

Iwao Ojima; Noriko Yoda

doi:10.1016/S0040-4039(00)87741-2

Synthesis of chiral tripeptides by asymmetric hydrogenation of dehydrotripeptides. Remarkable effects of N-protecting groups on stereoselectivity and reactivity

Iwao Ojima
, Noriko Yoda

Chemistry

Sagami Chemical Research Institute

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

18 Scopus citations

Abstract

Dehydrotripeptides, X- C *CH(Rⁱ)-ΔPhe- C *CH(R^k)COOMe (3: X = ^tBOC-NH,CBZ-NH, CF₃CONH and N₃), were employed for the asymmetric hydrogenation catalyzed by chiral rhodium complexes and it was found that ^tBOC-3 brought about by far the best results. Stereoselective dideuteration of a ^tBOC-3 was successfully performed.

Original language	English
Pages (from-to)	3913-3916
Number of pages	4
Journal	Tetrahedron Letters
Volume	23
Issue number	38
DOIs	https://doi.org/10.1016/S0040-4039(00)87741-2
State	Published - 1982

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title = "Synthesis of chiral tripeptides by asymmetric hydrogenation of dehydrotripeptides. Remarkable effects of N-protecting groups on stereoselectivity and reactivity",

abstract = "Dehydrotripeptides, X- C *CH(Ri)-ΔPhe- C *CH(Rk)COOMe (3: X = tBOC-NH,CBZ-NH, CF3CONH and N3), were employed for the asymmetric hydrogenation catalyzed by chiral rhodium complexes and it was found that tBOC-3 brought about by far the best results. Stereoselective dideuteration of a tBOC-3 was successfully performed.",

author = "Iwao Ojima and Noriko Yoda",

year = "1982",

doi = "10.1016/S0040-4039(00)87741-2",

language = "English",

volume = "23",

pages = "3913--3916",

journal = "Tetrahedron Letters",

issn = "0040-4039",

number = "38",

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TY - JOUR

T1 - Synthesis of chiral tripeptides by asymmetric hydrogenation of dehydrotripeptides. Remarkable effects of N-protecting groups on stereoselectivity and reactivity

AU - Ojima, Iwao

AU - Yoda, Noriko

PY - 1982

Y1 - 1982

N2 - Dehydrotripeptides, X- C *CH(Ri)-ΔPhe- C *CH(Rk)COOMe (3: X = tBOC-NH,CBZ-NH, CF3CONH and N3), were employed for the asymmetric hydrogenation catalyzed by chiral rhodium complexes and it was found that tBOC-3 brought about by far the best results. Stereoselective dideuteration of a tBOC-3 was successfully performed.

AB - Dehydrotripeptides, X- C *CH(Ri)-ΔPhe- C *CH(Rk)COOMe (3: X = tBOC-NH,CBZ-NH, CF3CONH and N3), were employed for the asymmetric hydrogenation catalyzed by chiral rhodium complexes and it was found that tBOC-3 brought about by far the best results. Stereoselective dideuteration of a tBOC-3 was successfully performed.

UR - https://www.scopus.com/pages/publications/0008552124

U2 - 10.1016/S0040-4039(00)87741-2

DO - 10.1016/S0040-4039(00)87741-2

M3 - Article

AN - SCOPUS:0008552124

SN - 0040-4039

VL - 23

SP - 3913

EP - 3916

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 38

ER -

Synthesis of chiral tripeptides by asymmetric hydrogenation of dehydrotripeptides. Remarkable effects of N-protecting groups on stereoselectivity and reactivity

Abstract

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