Stereochemistry of enantioselective deprotonation of 4-substituted cyclohexanones by chiral bidentate lithium amides

Masaharu Toriyama; Keizo Sugasawa; Mitsuru Shindo; Norio Tokutake; Kenji Koga

doi:10.1016/S0040-4039(96)02373-8

Stereochemistry of enantioselective deprotonation of 4-substituted cyclohexanones by chiral bidentate lithium amides

Masaharu Toriyama, Keizo Sugasawa, Mitsuru Shindo, Norio Tokutake, Kenji Koga

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

29 Citations (Scopus)

Abstract

Enantioselective deprotonation of 4-substituted cyclohexanones (1) in the presence of excess trimethylsilyl chloride was examined using chiral bidentate lithium amides ((R)-3~(R)-7 in THF. The solution structure of (R)-3a in THF in the presence and in the absence of lithium chloride were studied by NMR. It is concluded that the eight-membered cyclic transition state (10) offers reasonable explanation of the stereochemical course of the present reaction using (R)-3a.

Original language	English
Pages (from-to)	567-570
Number of pages	4
Journal	Tetrahedron Letters
Volume	38
Issue number	4
DOIs	https://doi.org/10.1016/S0040-4039(96)02373-8
Publication status	Published - Jan 27 1997
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(96)02373-8

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abstract = "Enantioselective deprotonation of 4-substituted cyclohexanones (1) in the presence of excess trimethylsilyl chloride was examined using chiral bidentate lithium amides ((R)-3~(R)-7 in THF. The solution structure of (R)-3a in THF in the presence and in the absence of lithium chloride were studied by NMR. It is concluded that the eight-membered cyclic transition state (10) offers reasonable explanation of the stereochemical course of the present reaction using (R)-3a.",

author = "Masaharu Toriyama and Keizo Sugasawa and Mitsuru Shindo and Norio Tokutake and Kenji Koga",

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T1 - Stereochemistry of enantioselective deprotonation of 4-substituted cyclohexanones by chiral bidentate lithium amides

AU - Toriyama, Masaharu

AU - Sugasawa, Keizo

AU - Shindo, Mitsuru

AU - Tokutake, Norio

AU - Koga, Kenji

PY - 1997/1/27

Y1 - 1997/1/27

N2 - Enantioselective deprotonation of 4-substituted cyclohexanones (1) in the presence of excess trimethylsilyl chloride was examined using chiral bidentate lithium amides ((R)-3~(R)-7 in THF. The solution structure of (R)-3a in THF in the presence and in the absence of lithium chloride were studied by NMR. It is concluded that the eight-membered cyclic transition state (10) offers reasonable explanation of the stereochemical course of the present reaction using (R)-3a.

AB - Enantioselective deprotonation of 4-substituted cyclohexanones (1) in the presence of excess trimethylsilyl chloride was examined using chiral bidentate lithium amides ((R)-3~(R)-7 in THF. The solution structure of (R)-3a in THF in the presence and in the absence of lithium chloride were studied by NMR. It is concluded that the eight-membered cyclic transition state (10) offers reasonable explanation of the stereochemical course of the present reaction using (R)-3a.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 4

ER -

Stereochemistry of enantioselective deprotonation of 4-substituted cyclohexanones by chiral bidentate lithium amides

Abstract

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