Lithium/Ammonia Cleavage of the N-N Bond in N-(MethoxycarbonyI)- and N-Acetylhydrazines

Scott E. Denmark; Olivier Nicaise; James P. Edwards

doi:10.1021/jo00312a034

Lithium/Ammonia Cleavage of the N-N Bond in N-(MethoxycarbonyI)- and N-Acetylhydrazines

Scott E. Denmark
, Olivier Nicaise
, James P. Edwards

Chemistry

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

Abstract

The diastereoselective addition of organocerium reagents to L-proline-derived hydrazones 1 has recently been reported from these laboratories¹(Scheme I). The reaction is compatible with a wide range of substrates (R¹= Ph, PhCH_2,PhCH₂CH₂, (E)-CH₃CH=CH) and accommodates a variety of unstabilized nucleophiles (R³= Me, n-Bu, i-Pr, t-Bu, Ph, i-Pr₃SiCH=CH) derived from either lithium or halomagnesium precursors. The additions proceed in good yield (67-81%) and with high diastereoselectivity (>93:7 ds).

Original language	English (US)
Pages (from-to)	6219-6223
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	55
Issue number	25
DOIs	https://doi.org/10.1021/jo00312a034
State	Published - Dec 1990

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Organic Chemistry

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10.1021/jo00312a034

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title = "Lithium/Ammonia Cleavage of the N-N Bond in N-(MethoxycarbonyI)- and N-Acetylhydrazines",

abstract = "The diastereoselective addition of organocerium reagents to L-proline-derived hydrazones 1 has recently been reported from these laboratories1(Scheme I). The reaction is compatible with a wide range of substrates (R1= Ph, PhCH2,PhCH2CH2, (E)-CH3CH=CH) and accommodates a variety of unstabilized nucleophiles (R3= Me, n-Bu, i-Pr, t-Bu, Ph, i-Pr3SiCH=CH) derived from either lithium or halomagnesium precursors. The additions proceed in good yield (67-81\%) and with high diastereoselectivity (>93:7 ds).",

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year = "1990",

month = dec,

doi = "10.1021/jo00312a034",

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volume = "55",

pages = "6219--6223",

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publisher = "American Chemical Society",

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AU - Denmark, Scott E.

AU - Nicaise, Olivier

AU - Edwards, James P.

PY - 1990/12

Y1 - 1990/12

N2 - The diastereoselective addition of organocerium reagents to L-proline-derived hydrazones 1 has recently been reported from these laboratories1(Scheme I). The reaction is compatible with a wide range of substrates (R1= Ph, PhCH2,PhCH2CH2, (E)-CH3CH=CH) and accommodates a variety of unstabilized nucleophiles (R3= Me, n-Bu, i-Pr, t-Bu, Ph, i-Pr3SiCH=CH) derived from either lithium or halomagnesium precursors. The additions proceed in good yield (67-81%) and with high diastereoselectivity (>93:7 ds).

AB - The diastereoselective addition of organocerium reagents to L-proline-derived hydrazones 1 has recently been reported from these laboratories1(Scheme I). The reaction is compatible with a wide range of substrates (R1= Ph, PhCH2,PhCH2CH2, (E)-CH3CH=CH) and accommodates a variety of unstabilized nucleophiles (R3= Me, n-Bu, i-Pr, t-Bu, Ph, i-Pr3SiCH=CH) derived from either lithium or halomagnesium precursors. The additions proceed in good yield (67-81%) and with high diastereoselectivity (>93:7 ds).

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VL - 55

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JF - Journal of Organic Chemistry

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ER -

Lithium/Ammonia Cleavage of the N-N Bond in N-(MethoxycarbonyI)- and N-Acetylhydrazines

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