Transition metal-catalyzed diastereoselective aldol reactions of prochiral ketones with methyl isocyanoacetate

Vadim A. Soloshonok; Alexey D. Kacharov; Dimitry V. Avilov; Tamio Hayashi

doi:10.1016/0040-4039(96)01746-7

Transition metal-catalyzed diastereoselective aldol reactions of prochiral ketones with methyl isocyanoacetate

Vadim A. Soloshonok, Alexey D. Kacharov, Dimitry V. Avilov, Tamio Hayashi

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Abstract

Systematic study of the transition metal-catalyzed aldol reactions of certain prochiral ketones with methyl isocyanoacetate has been made. High diastereoselectivity (80-98% de) of these condensations, leading to methyl (4R*,5R*)-4,5-dihydro-5,5-(disubstituted)-4-oxazolecarboxylates was shown to be controlled by the nature of both catalyst and substituents on the starting ketone.

Original language	English (US)
Pages (from-to)	7845-7848
Number of pages	4
Journal	Tetrahedron Letters
Volume	37
Issue number	43
DOIs	https://doi.org/10.1016/0040-4039(96)01746-7
State	Published - Oct 21 1996
Externally published	Yes

Bibliographical note

Funding Information:
Acknowledgment. We thank the JSPS Foundation (Japan), Ministry of Education, Japan, for a Grant-in-Aid for Scientific Research, Uehara Memorial Foundation, International Science Foundation (U6M000, U6M200), INTAS (Network 93-799) for partial financial support of this work.

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title = "Transition metal-catalyzed diastereoselective aldol reactions of prochiral ketones with methyl isocyanoacetate",

abstract = "Systematic study of the transition metal-catalyzed aldol reactions of certain prochiral ketones with methyl isocyanoacetate has been made. High diastereoselectivity (80-98% de) of these condensations, leading to methyl (4R*,5R*)-4,5-dihydro-5,5-(disubstituted)-4-oxazolecarboxylates was shown to be controlled by the nature of both catalyst and substituents on the starting ketone.",

author = "Soloshonok, {Vadim A.} and Kacharov, {Alexey D.} and Avilov, {Dimitry V.} and Tamio Hayashi",

note = "Funding Information: Acknowledgment. We thank the JSPS Foundation (Japan), Ministry of Education, Japan, for a Grant-in-Aid for Scientific Research, Uehara Memorial Foundation, International Science Foundation (U6M000, U6M200), INTAS (Network 93-799) for partial financial support of this work.",

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T1 - Transition metal-catalyzed diastereoselective aldol reactions of prochiral ketones with methyl isocyanoacetate

AU - Soloshonok, Vadim A.

AU - Kacharov, Alexey D.

AU - Avilov, Dimitry V.

AU - Hayashi, Tamio

N1 - Funding Information: Acknowledgment. We thank the JSPS Foundation (Japan), Ministry of Education, Japan, for a Grant-in-Aid for Scientific Research, Uehara Memorial Foundation, International Science Foundation (U6M000, U6M200), INTAS (Network 93-799) for partial financial support of this work.

PY - 1996/10/21

Y1 - 1996/10/21

N2 - Systematic study of the transition metal-catalyzed aldol reactions of certain prochiral ketones with methyl isocyanoacetate has been made. High diastereoselectivity (80-98% de) of these condensations, leading to methyl (4R*,5R*)-4,5-dihydro-5,5-(disubstituted)-4-oxazolecarboxylates was shown to be controlled by the nature of both catalyst and substituents on the starting ketone.

AB - Systematic study of the transition metal-catalyzed aldol reactions of certain prochiral ketones with methyl isocyanoacetate has been made. High diastereoselectivity (80-98% de) of these condensations, leading to methyl (4R*,5R*)-4,5-dihydro-5,5-(disubstituted)-4-oxazolecarboxylates was shown to be controlled by the nature of both catalyst and substituents on the starting ketone.

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JF - Tetrahedron Letters

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ER -

Transition metal-catalyzed diastereoselective aldol reactions of prochiral ketones with methyl isocyanoacetate

Abstract

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