Chiral α,β-Dialkoxy- and α-Alkoxy-β-aminostannanes: Preparation and Copper-Mediated Cross-Coupling

Suchismita Mohapatra; A. Bandyopadhyay; D. K. Barma; Jorge H. Capdevila; J. R. Falck

doi:10.1021/ol035458v

Chiral α,β-Dialkoxy- and α-Alkoxy-β-aminostannanes: Preparation and Copper-Mediated Cross-Coupling

Suchismita Mohapatra, A. Bandyopadhyay, D. K. Barma, Jorge H. Capdevila, J. R. Falck

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Abstract

(Equation Presented) Addition of Zn(n-Bu₃Sn)₂ to prochiral aldehydes affords anti-α,β-dialkoxy- and anti-α-alkoxy-β-aminostannanes in good yield (up to 77%) and excellent diastereoselectivity (up to 98% de), syn-lsomers are accessed from the initial adducts via Mitsunobu inversion/saponification. The corresponding thionocarbamates undergo mild Cu(l)-mediated cross-coupling with a variety of organic halides, inter alia, allylic, cinnamylic, propargylic, and acetylenic, with retention of configuration.

Original language	English
Pages (from-to)	4759-4762
Number of pages	4
Journal	Organic Letters
Volume	5
Issue number	25
DOIs	https://doi.org/10.1021/ol035458v
State	Published - 11 Dec 2003

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title = "Chiral α,β-Dialkoxy- and α-Alkoxy-β-aminostannanes: Preparation and Copper-Mediated Cross-Coupling",

abstract = "(Equation Presented) Addition of Zn(n-Bu3Sn)2 to prochiral aldehydes affords anti-α,β-dialkoxy- and anti-α-alkoxy-β-aminostannanes in good yield (up to 77%) and excellent diastereoselectivity (up to 98% de), syn-lsomers are accessed from the initial adducts via Mitsunobu inversion/saponification. The corresponding thionocarbamates undergo mild Cu(l)-mediated cross-coupling with a variety of organic halides, inter alia, allylic, cinnamylic, propargylic, and acetylenic, with retention of configuration.",

author = "Suchismita Mohapatra and A. Bandyopadhyay and Barma, {D. K.} and Capdevila, {Jorge H.} and Falck, {J. R.}",

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T1 - Chiral α,β-Dialkoxy- and α-Alkoxy-β-aminostannanes

T2 - Preparation and Copper-Mediated Cross-Coupling

AU - Mohapatra, Suchismita

AU - Bandyopadhyay, A.

AU - Barma, D. K.

AU - Capdevila, Jorge H.

AU - Falck, J. R.

PY - 2003/12/11

Y1 - 2003/12/11

N2 - (Equation Presented) Addition of Zn(n-Bu3Sn)2 to prochiral aldehydes affords anti-α,β-dialkoxy- and anti-α-alkoxy-β-aminostannanes in good yield (up to 77%) and excellent diastereoselectivity (up to 98% de), syn-lsomers are accessed from the initial adducts via Mitsunobu inversion/saponification. The corresponding thionocarbamates undergo mild Cu(l)-mediated cross-coupling with a variety of organic halides, inter alia, allylic, cinnamylic, propargylic, and acetylenic, with retention of configuration.

AB - (Equation Presented) Addition of Zn(n-Bu3Sn)2 to prochiral aldehydes affords anti-α,β-dialkoxy- and anti-α-alkoxy-β-aminostannanes in good yield (up to 77%) and excellent diastereoselectivity (up to 98% de), syn-lsomers are accessed from the initial adducts via Mitsunobu inversion/saponification. The corresponding thionocarbamates undergo mild Cu(l)-mediated cross-coupling with a variety of organic halides, inter alia, allylic, cinnamylic, propargylic, and acetylenic, with retention of configuration.

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U2 - 10.1021/ol035458v

DO - 10.1021/ol035458v

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AN - SCOPUS:0345967845

SN - 1523-7060

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JO - Organic Letters

JF - Organic Letters

IS - 25

ER -

Chiral α,β-Dialkoxy- and α-Alkoxy-β-aminostannanes: Preparation and Copper-Mediated Cross-Coupling

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