An efficient procedure for the synthesis of 2-N-Boc-amino-3,5-diols

Dias, Luiz C.; Fattori, Juliana; Perez, Carla Cristina; Oliveira, Vanda; Aguilar, Andrea M.

doi:10.1016/j.tet.2008.04.049

Cited by 17 publications

(12 citation statements)

References 64 publications

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“…[3][4][5][6][7][8][9][10][11]14 According to previously established experimental procedures, the allylsilanes were mixed with SnCl 4 (1.0 equiv. in CH 2 Cl 2 ) before the addition of a solution of the aldehyde in order to promote the SiMe 3 /SnCl 3 exchange leading to the corresponding allyltrichlorostannanes 5-8 (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

“…5 For allylsilane 2 the SiMe 3 /SnCl 3 exchange to give 6 and Me 3 SiCl is faster, as expected for a 1,1-disubstituted electron-rich olefin, being complete after 10 minutes at room temperature. 14 3 , at −60 o C, slightly yellow homogeneous solutions were obtained. The resulting NMR spectrum at −60 o C showed formation of Me 3 SiCl and complete consumption of both allylsilanes within less than 1 minute to give allyltrichlorostannanes (R)-7 and (S)-8, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…5 The same trend is observed for allylstannane 6 when compared to allylsilane 2 ( Table 2). 14 In the case of (R)-7, the deshielding of the hydrogens H 6 to H 9 in the 1 H NMR spectrum provides the best diagnostics ( Table 3). The methylenic hydrogens H 6 and H 7 as well as the benzylic hydrogens H 8 and H 9 are too far away from the trichlorotin group to suffer from inductive effects.…”

Section: Resultsmentioning

confidence: 99%

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Addition of chiral and achiral allyltrichlorostannanes to chiral±-alkoxy aldehydes

Dias

Augusto

Perez

et al. 2009

J. Braz. Chem. Soc.

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Aliltricloroestananas quirais e aquirais reagem com α-alcóxi aldeídos quirais para fornecer alcoóis homoalílicos com moderados a bons níveis de diastereosseletividade 1,4-syn.Achiral and chiral allyltrichlorostannanes reacted with chiral α-alkoxy aldehydes to give the corresponding homoallylic alcohols with moderate to good levels of 1,4-syn-diastereoselection. Keywords: allyltrichlorostannanes, allylsilanes, homoallylic alcohols IntroductionAllylsilanes and allylstannanes are among the most important groups of organometallic-type reagents available for the control of acyclic stereochemistry and their reaction with aldehydes in the presence of Lewis acids is an important procedure for the preparation of homoallylic alcohols. 1,2The addition of allylstannanes bearing a stereogenic center to chiral aldehydes is particularly interesting in organic synthesis. We recently communicated that in situ prepared chiral allyltrichlorostannanes react with chiral aldehydes to give 1,4-syn homoallylic alcohols with high levels of diastereoselectivity. [3][4][5][6][7][8][9][10][11] We wish to describe here a stereocontrolled reaction between achiral and chiral allyltrichlorostannanes with chiral lactate-derived aldehydes to give fragments which can be found in a large variety of naturally-occurring products with promising biological activities. 12 This study details our efforts to understand the double stereodifferentiating stereocontrol elements involved in chiral allyltrichlorostannane additions to chiral aldehydes. 13 Results and DiscussionAchiral and chiral allylsilanes 1-4 were prepared from the corresponding easily available methyl esters, as described in previous papers from this laboratory (Scheme 1). [3][4][5][6][7][8][9][10][11]14 According to previously established experimental procedures, the allylsilanes were mixed with SnCl 4 (1.0 equiv. in CH 2 Cl 2 ) before the addition of a solution of the aldehyde in order to promote the SiMe 3 /SnCl 3 exchange leading to the corresponding allyltrichlorostannanes 5-8 (Scheme 1). 5To the best of our knowledge, the first spectroscopic information available on exchange reactions involving allylsilanes and SnCl 4 was reported by Denmark and co-workers in 1988.13 In 1999, we described the first direct evidence for interaction between SnCl 4 and chiral allylic silane 3 bearing an ether functionality that generated a new species by means of NMR spectroscopy.5 In a continuation of these initial studies we have done a spectroscopic study ( For allyltrimethylsilane 1 the SiMe 3 /SnCl 3 exchange producing allyltrichlorostannane 5 and Me 3 SiCl is complete after 2 h at room temperature (Scheme 1). 5 For allylsilane 2 the SiMe 3 /SnCl 3 exchange to give 6 and Me 3 SiCl is faster, as expected for a 1,1-disubstituted electron-rich olefin, being complete after 10 minutes at room temperature. o C showed formation of Me 3 SiCl and complete consumption of both allylsilanes within less than 1 minute to give allyltrichlorostannanes (R)-7 and (S)-8, respectively. It appears that the oxygen function...

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Addition of chiral and achiral allyltrichlorostannanes to chiral±-alkoxy aldehydes

Dias

Augusto

Perez

et al. 2009

J. Braz. Chem. Soc.

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“…Chiral aminodiols and their derivatives also find application as catalysts for enantioselective transformations [9,10]. Different approaches to obtain aminodiol derivatives have been developed [11][12][13]. Aminolysis of 1,2-epoxides represents one of the valuable pathway to produce commercially important aminoalcohols and aminodiols from olefins [14][15][16].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of (1S,2R,4S)-1-((phenylamino)methyl)- 4-(prop-1-en-2-yl)cyclohexane-1,2-diol), C16H23NO2

Outouch¹,

Boualy²,

Firdoussi³

et al. 2011

Zeitschrift Für Kristallographie - New Crystal Structures

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“…The treatment of 20 with 2,2-dimethoxypropane 13 and catalytic amounts of CSA resulted in the formation of the corresponding isopropylidene derivative 21 in 81% yield (Scheme 4). Cleavage of the acetate in 21 was achieved by employing sodium ethoxide in ethanol to give alcohol 22 (92%, Scheme 4).…”

Section: Synthesis Of the Key Alcohol 25mentioning

confidence: 99%

Total synthesis of a protected form of sphingofungin E using the [3,3]-sigmatropic rearrangement of an allylic thiocyanate as the key reaction

Martinková¹,

Gonda²,

Raschmanová³

et al. 2010

Carbohydrate Research

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An efficient procedure for the synthesis of 2-N-Boc-amino-3,5-diols

Cited by 17 publications

References 64 publications

Addition of chiral and achiral allyltrichlorostannanes to chiral±-alkoxy aldehydes

Addition of chiral and achiral allyltrichlorostannanes to chiral±-alkoxy aldehydes

Crystal structure of (1S,2R,4S)-1-((phenylamino)methyl)- 4-(prop-1-en-2-yl)cyclohexane-1,2-diol), C16H23NO2

Total synthesis of a protected form of sphingofungin E using the [3,3]-sigmatropic rearrangement of an allylic thiocyanate as the key reaction

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