Solid state and solution structural studies of chiral phosphoramide-tin complexes relevant to Lewis base catalyzed aldol reactions

Scott E. Denmark; Xiping Su

doi:10.1016/S0040-4020(99)00439-1

Solid state and solution structural studies of chiral phosphoramide-tin complexes relevant to Lewis base catalyzed aldol reactions

Scott E. Denmark, Xiping Su

Chemistry

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

Abstract

Complexes of chiral phosphoramides 4 and 5 with tin-based Lewis acids were studied by both X-ray crystallography and low temperature ¹¹⁹Sn NMR spectroscopy. The structure of a ternary complex between 5, SnCl₄ and benzaldehyde was also obtained and provided a detailed view of the binding of both aldehyde and phosphoramide to Lewis acids. ¹¹⁹Sn NMR, spectroscopy indicated that a 2/1 stoichiometry of phosphoramide to tin is favored in solution as well.

Original language	English (US)
Pages (from-to)	8727-8738
Number of pages	12
Journal	Tetrahedron
Volume	55
Issue number	29
DOIs	https://doi.org/10.1016/S0040-4020(99)00439-1
State	Published - Jul 16 1999

Keywords

Aldol Reactions
Phosphoramides
Tin and Compounds
X-Ray Crystal Structures

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Online availability

10.1016/S0040-4020(99)00439-1

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abstract = "Complexes of chiral phosphoramides 4 and 5 with tin-based Lewis acids were studied by both X-ray crystallography and low temperature 119Sn NMR spectroscopy. The structure of a ternary complex between 5, SnCl4 and benzaldehyde was also obtained and provided a detailed view of the binding of both aldehyde and phosphoramide to Lewis acids. 119Sn NMR, spectroscopy indicated that a 2/1 stoichiometry of phosphoramide to tin is favored in solution as well.",

keywords = "Aldol Reactions, Phosphoramides, Tin and Compounds, X-Ray Crystal Structures",

author = "Denmark, {Scott E.} and Xiping Su",

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T1 - Solid state and solution structural studies of chiral phosphoramide-tin complexes relevant to Lewis base catalyzed aldol reactions

AU - Denmark, Scott E.

AU - Su, Xiping

PY - 1999/7/16

Y1 - 1999/7/16

N2 - Complexes of chiral phosphoramides 4 and 5 with tin-based Lewis acids were studied by both X-ray crystallography and low temperature 119Sn NMR spectroscopy. The structure of a ternary complex between 5, SnCl4 and benzaldehyde was also obtained and provided a detailed view of the binding of both aldehyde and phosphoramide to Lewis acids. 119Sn NMR, spectroscopy indicated that a 2/1 stoichiometry of phosphoramide to tin is favored in solution as well.

AB - Complexes of chiral phosphoramides 4 and 5 with tin-based Lewis acids were studied by both X-ray crystallography and low temperature 119Sn NMR spectroscopy. The structure of a ternary complex between 5, SnCl4 and benzaldehyde was also obtained and provided a detailed view of the binding of both aldehyde and phosphoramide to Lewis acids. 119Sn NMR, spectroscopy indicated that a 2/1 stoichiometry of phosphoramide to tin is favored in solution as well.

KW - Aldol Reactions

KW - Phosphoramides

KW - Tin and Compounds

KW - X-Ray Crystal Structures

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VL - 55

SP - 8727

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JO - Tetrahedron

JF - Tetrahedron

IS - 29

ER -

Solid state and solution structural studies of chiral phosphoramide-tin complexes relevant to Lewis base catalyzed aldol reactions

Abstract

Keywords

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