Asymmetric synthesis of γ-perfluoroalkyl(aryl) butyrolactones via organoboranes

Ramachandran, P. Veeraraghavan; Padiya, Kamlesh J.; Rauniyar, Vivek; Reddy, M. Venkat Ram; Brown, Herbert C.

doi:10.1016/j.tetlet.2003.11.050

Cited by 37 publications

(15 citation statements)

References 18 publications

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“…Partially fluorinated analogues of biologically important compounds bring about dramatic changes and distinctive modifications in their biological activities; this makes it more necessary to establish the efficient methods for the synthesis of selectively fluorinated compounds [1]. We are interested in the synthesis of fluorinated g-lactones, which are important synthons that display more unique biologically active properties in organic chemistry [2].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of α,α-difluoro-γ-butyrolactones via ethyl iododifluoroacetate

Xiao

Shen

et al. 2005

Journal of Fluorine Chemistry

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Section: Introductionmentioning

confidence: 99%

Synthesis of α,α-difluoro-γ-butyrolactones via ethyl iododifluoroacetate

Xiao

Shen

et al. 2005

Journal of Fluorine Chemistry

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“…We had recently reported similar alkoxyallylboration of fluoral with "ate" complex VII. [27] We do not know the exact mechanism of the crotylboration with the "ate" complex. The 11 B NMR spectrum of the reaction mixture containing 1 a and V showed a peak at d 4, corresponding to the "ate" complex [18c] and in 1 H NMR spectrum there was a peak at d 9.0, corresponding to the unreacted N-silylimine.…”

Section: Resultsmentioning

confidence: 99%

Highly Diastereoselective and Enantioselective Preparation of Homoallylic Amines: Application for the Synthesis of β‐Amino Acids and γ‐Lactams

Ramachandran

Burghardt

2005

Chemistry A European J

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Reactions of N-silyl- and N-aluminoimines with B-allyldiisopinocampheylborane in the presence of methanol, followed by oxidative workup furnished homoallylic amines in good yields and high ee. A 11B NMR spectroscopy study revealed that the reactions do not proceed, even at room temperature, unless a molar equivalent of water or methanol is added. The first reagent-controlled asymmetric crotylboration and alkoxyallylboration of aldimines furnishing beta-methyl or beta-alkoxy homoallylic amines in very high diastereoselectivity and enantioselectivity are reported herein. Crotylboration and alkoxyallylboration of imines proceed only with the "allyl"-boron "ate" complexes, instead of the "allyl"-dialkylboron reagents used with aldehydes. The addition of methanol is necessary for these reactions as well. Application of this methodology for the conversion of representative nitriles to beta-amino acids in two steps has been described. Additionally, a procedure for the preparation of chiral delta-amino alcohols and gamma-lactams from nitriles is also reported.

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“…Extension of alkoxyallylboration to perfluoroaldehydes, provided the fluoro-homoallylic alcohols 116 which were eventually converted to the fluorinated γ-lactones 117 and δ-lactones 118 in 2-3 steps (Scheme 31). 45 A trifluoromethyl analog of blastmycinolactol 121 was also synthesized starting the homoallylic alcohol 120 derived from alkoxyallylboration of trifluoroacetaldehyde 119 (Scheme 32). Recently, Curran and coworkers utilized the alkoxyallylboration of n-tridecanal with both antipodes of B-γ-alkoxyallyldiisopinocampheylborane for the synthesis of (S, S) and (R, R) 1,2-syn α-alkoxy homoallylic alcohols syn-126.…”

Section: Applications Of (B)-(z)-γ-[(2-methoxyethoxymethoxy)allyl]diimentioning

confidence: 99%

Stereoselective allylboration using (B)-γ-alkoxyallyldiisopinocampheylboranes: highly selective reactions for organic synthesis

Chandra¹,

Reddy²

2007

Arkivoc

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This review describes the synthesis of novel alkoxyallylborane reagents derived from α-pinene and their applications in stereoselective total synthesis of natural products. These reagents can be conveniently prepared and react readily with a wide variety of aldehydes and imines to provide the corresponding α-alkoxy substituted homoallylic alcohols/amines respectively. The (Z)-γ-alkoxyallylborane reagents provide 1,2-syn α-alkoxy homoallylic alcohols/amines while the corresponding (E)-γ-alkoxyallylborane reagents furnish 1,2-anti products exclusively in very high enantioselectivities.

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Asymmetric synthesis of γ-perfluoroalkyl(aryl) butyrolactones via organoboranes

Cited by 37 publications

References 18 publications

Synthesis of α,α-difluoro-γ-butyrolactones via ethyl iododifluoroacetate

Synthesis of α,α-difluoro-γ-butyrolactones via ethyl iododifluoroacetate

Highly Diastereoselective and Enantioselective Preparation of Homoallylic Amines: Application for the Synthesis of β‐Amino Acids and γ‐Lactams

Stereoselective allylboration using (B)-γ-alkoxyallyldiisopinocampheylboranes: highly selective reactions for organic synthesis

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