Stereoselective synthesis of sphinganine by means of modified asymmetric borane reduction

Masui, Masao; Shioiri, Takayuki

doi:10.1016/s0040-4039(98)01020-x

Cited by 33 publications

(14 citation statements)

References 4 publications

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“…The modified procedure for asymmetric borane reduction is applicable to the stereoselective synthesis of Nbenzoylsphinganine. 5 Reduction of α-oxoketoxime trityl ethers 1 and 2 using catalyst prepared in situ from (1R,2R,3S,5R)-ATBH and trimethyl borate proceeds in high yields with high enantioselectivities (eq 6). Satisfactory results are obtained by employing the borane-N,N-diethylaniline complex as a reducing agent.…”

Section: Moriyasu Masuimentioning

confidence: 99%

3-Amino-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol

Masui

Krzemiński

2014

Encyclopedia of Reagents for Organic Synthesis

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Section: Moriyasu Masuimentioning

confidence: 99%

3-Amino-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol

Masui

Krzemiński

2014

Encyclopedia of Reagents for Organic Synthesis

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“…One requires the insertion of the alcohol and amino groups in the α,β position with the correct stereochemistry [17][18][19][20]. The second strategy involves a bond formation between two chiral centers to produce the targeted 2-amino-1,3-diol [21,22]. For instance, deoxoprosophylline (5) as a cyclic 2-amino-1,3-diol target molecule was prepared by Kokatla et al in an 8 step synthesis starting from Perlin aldehydes, via Pd(OH) 2 -catalyzed reductive azidoketon cyclisation [23].…”

Section: Introductionmentioning

confidence: 99%

Stereoselective synthesis and transformation of pinane-based 2-amino-1,3-diols

Bajtel

Raji

Haukka

et al. 2021

Beilstein J. Org. Chem.

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A library of pinane-based 2-amino-1,3-diols was synthesised in a stereoselective manner. Isopinocarveol prepared from (−)-α-pinene was converted into condensed oxazolidin-2-one in two steps by carbamate formation followed by a stereoselective aminohydroxylation process. The relative stereochemistry of the pinane-fused oxazolidin-2-one was determined by 2D NMR and X-ray spectroscopic techniques. The regioisomeric spiro-oxazolidin-2-one was prepared in a similar way starting from the commercially available (1R)-(−)-myrtenol (10). The reduction or alkaline hydrolysis of the oxazolidines, followed by reductive alkylation resulted in primary and secondary 2-amino-1,3-diols, which underwent a regioselective ring closure with formaldehyde or benzaldehyde delivering pinane-condensed oxazolidines. During the preparation of 2-phenyliminooxazolidine, an interesting ring–ring tautomerism was observed in CDCl3.

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“…One requires the insertion of the alcohol and amino groups in the α,β position according to the correct stereochemistry [18][19][20][21]. The second strategy involves bond formation between two chiral centres to produce the targeted 2-amino-1,3-diol [22,23]. For instance, Michael addition followed by intramolecular cyclisation of alkynone and the γ-amino alcohol moiety followed by diastereoselective hydrogenation can afford a cyclic 2-amino-1,3-diol such as Deoxoprosophylline (5).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and transformation of sphingosine analogue pinane-based 2-amino-1,3-diols

Bajtel¹,

Raji²,

Haukka³

et al. 2021

Preprint

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A library of pinane-based 2-amino-1,3-diols, analogues of biologically active sphingosine, was synthesised in a stereoselective manner. Isopinocarveol prepared from (–)-α-pinene was converted to condensed oxazolidin-2-one in two steps by carbamate formation followed by a stereoselective aminohydroxylation process. The relative stereochemistry of the pinane-fused oxazolidin-2-one was determined by 2D NMR and X-ray technics. The regioisomeric spiro-oxazolidin-2-one was prepared in a similar way starting from commercially available (1R)-(–)-myrtenol. Reduction or alkaline hydrolysis of oxazolidines followed by reductive alkylation resulted in primary and secondary 2-amino-1,3-diols, which underwent regioselective ring closure with formaldehyde or benzaldehyde delivering pinane-condensed oxazolidines. During the preparation of 2-phenyliminooxazolidine, an interesting ring–ring tautomerism was observed in CDCl3.

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Stereoselective synthesis of sphinganine by means of modified asymmetric borane reduction

Cited by 33 publications

References 4 publications

3-Amino-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol

3-Amino-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol

Stereoselective synthesis and transformation of pinane-based 2-amino-1,3-diols

Synthesis and transformation of sphingosine analogue pinane-based 2-amino-1,3-diols

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