Solution structures of a monodentate chiral lithium amide in the presence of lithium halide

Keizo Sugasawa; Mitsuru Shindo; Hiroshi Noguchi; Kenji Koga

doi:10.1016/0040-4039(96)01681-4

Solution structures of a monodentate chiral lithium amide in the presence of lithium halide

Keizo Sugasawa, Mitsuru Shindo, Hiroshi Noguchi, Kenji Koga

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

65 Citations (Scopus)

Abstract

Enantioselectivity of deprotonation reaction of 4-tert-butylcyclohexanone (2) by a monodentate chiral lithium amide ((R,R)-1) in THF is strongly influenced by the presence of lithium halides. Aggregation states of this chiral lithium amide in THF-d₈ in the absence and in the presence of lithium halides were studied by ⁶Li and ¹⁵N NMR. It is concluded that the mixed dimer (D) is the species to give the high enantioselectivity of the reaction.

Original language	English
Pages (from-to)	7377-7380
Number of pages	4
Journal	Tetrahedron Letters
Volume	37
Issue number	41
DOIs	https://doi.org/10.1016/0040-4039(96)01681-4
Publication status	Published - Oct 7 1996
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Solution structures of a monodentate chiral lithium amide in the presence of lithium halide",

abstract = "Enantioselectivity of deprotonation reaction of 4-tert-butylcyclohexanone (2) by a monodentate chiral lithium amide ((R,R)-1) in THF is strongly influenced by the presence of lithium halides. Aggregation states of this chiral lithium amide in THF-d8 in the absence and in the presence of lithium halides were studied by 6Li and 15N NMR. It is concluded that the mixed dimer (D) is the species to give the high enantioselectivity of the reaction.",

author = "Keizo Sugasawa and Mitsuru Shindo and Hiroshi Noguchi and Kenji Koga",

year = "1996",

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T1 - Solution structures of a monodentate chiral lithium amide in the presence of lithium halide

AU - Sugasawa, Keizo

AU - Shindo, Mitsuru

AU - Noguchi, Hiroshi

AU - Koga, Kenji

PY - 1996/10/7

Y1 - 1996/10/7

N2 - Enantioselectivity of deprotonation reaction of 4-tert-butylcyclohexanone (2) by a monodentate chiral lithium amide ((R,R)-1) in THF is strongly influenced by the presence of lithium halides. Aggregation states of this chiral lithium amide in THF-d8 in the absence and in the presence of lithium halides were studied by 6Li and 15N NMR. It is concluded that the mixed dimer (D) is the species to give the high enantioselectivity of the reaction.

AB - Enantioselectivity of deprotonation reaction of 4-tert-butylcyclohexanone (2) by a monodentate chiral lithium amide ((R,R)-1) in THF is strongly influenced by the presence of lithium halides. Aggregation states of this chiral lithium amide in THF-d8 in the absence and in the presence of lithium halides were studied by 6Li and 15N NMR. It is concluded that the mixed dimer (D) is the species to give the high enantioselectivity of the reaction.

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U2 - 10.1016/0040-4039(96)01681-4

DO - 10.1016/0040-4039(96)01681-4

M3 - Article

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VL - 37

SP - 7377

EP - 7380

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 41

ER -

Solution structures of a monodentate chiral lithium amide in the presence of lithium halide

Abstract

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