Synthesis and reactivity of cyclic sulfamidites and sulfamidates

Meléndez, Rosa E.; Lubell, William D.

doi:10.1016/s0040-4020(03)00284-9

Cited by 193 publications

(110 citation statements)

References 60 publications

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“…These unusual heterocycles have enjoyed only sparing use despite their potential as electrophilic azetidine equivalents. By contrast, five-membered ring sulfamidates and cyclic sulfates are broadly recognized as important functional surrogates of aziridines and epoxides, respectively [118][119][120][121]. However, the facility by which such heterocycles undergo nucleophilic ring opening is in no way mirrored by the robust oxathiazinanes.…”

Section: -Oxathiazinane-22-dioxides As Tools In Synthesismentioning

confidence: 99%

“…Two early reports of oxathiazinane ring opening seemed to indicate that only forcing conditions could promote C-O bond cleavage in these materials [122,123]. Fortunately, as both Du Bois and Lubell have shown, modification of the N-H moiety on the oxathiazinane ring with either acyl or alkyl groups (that is, to form 9-fluorenyl) can have a dramatic influence on the reactivity of these heterocycles [68,121,124]. As an example, ring opening of N-CBzoxathiazinane 134 occurs smoothly between 25 and 40 8C with nucleophiles that include CN -, N 3 -, thiolates, carboxylates, metal enolates, alcohols, and H 2 O (Scheme 17.40).…”

Section: -Oxathiazinane-22-dioxides As Tools In Synthesismentioning

confidence: 99%

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Rhodium(II)‐Catalyzed Oxidative Amination

Espino

Bois

2005

Modern Rhodium‐Catalyzed Organic Reactions

105

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17 Rhodium(II)-Catalyzed Oxidative Amination 380 Scheme 17.1 Copper-catalyzed decomposition of arylsulfonyl azides. Scheme 17.2 Intramolecular C-H amination of an iminoiodinane. 17.3 Intermolecular C-H Amination with Rhodium(II) Catalysts 381 Scheme 17.3 Metal porphyrin-catalyzed allylic amination. Scheme 17.4 C-H amination by a radical-rebound mechanism. 17 Rhodium(II)-Catalyzed Oxidative Amination 382 Scheme 17.5 Rhodium-catalyzed N-atom transfer using NsN=IPh. Scheme 17.6 Stereospecific C-H amination under rhodium-catalyzed conditions. 17.3 Intermolecular C-H Amination with Rhodium(II) Catalysts 383 Scheme 17.7 Radical clock study of metallo-nitrene C-H insertion. Scheme 17.8 Intermolecular C-H insertion by chiral rhodium catalysts. 17.5 Intramolecular C-H Amination with Rhodium(II) Catalysts 385 Scheme 17.11 Allylic and benzylic amination using PhI(OAc) 2 . 17.5 Intramolecular C-H Amination with Rhodium(II) Catalysts 387 Tab. 17.1 C-H amination of 18 carbamate esters. Entry Substrate Product Entry Substrate Product 17.5 Intramolecular C-H Amination with Rhodium(II) Catalysts 389 Scheme 17.14 Ketone formation by 28 alcohol-derived carbamates. 17.7 Enantioselective C-H Insertion with Sulfamate Esters 401 Scheme 17.29 Oxidative cyclization of unsaturated sulfonamides. Scheme 17.30 Preliminary investigations of asymmetric C-H amination. 17.11 Applications of C-H Amination in Synthesis 407 17.11 Applications of C-H Amination in Synthesis 409 Scheme 17.39 Asymmetric synthesis of (-)-tetrodotoxin. 17 Rhodium(II)-Catalyzed Oxidative Amination 410 Scheme 17.40 Nucleophilic ring opening of N-acylated oxathiazinanes. Scheme 17.41 Nickel-catalyzed cross-coupling of phenol-derived sulfamate esters.

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Section: -Oxathiazinane-22-dioxides As Tools In Synthesismentioning

confidence: 99%

Section: -Oxathiazinane-22-dioxides As Tools In Synthesismentioning

confidence: 99%

Rhodium(II)‐Catalyzed Oxidative Amination

Espino

Bois

2005

Modern Rhodium‐Catalyzed Organic Reactions

105

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“…After preparation of sulfamidate [12] 5 a,b nucleophilic attack using boc-mesidine [13] leads to 6 a,b. In case of bromo-substituted diamine 6 b, a phenyl substituent can be introduced by Suzuki coupling.…”

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confidence: 99%

Highly Active Chiral Ruthenium‐Based Metathesis Catalysts through a Monosubstitution in the N‐Heterocyclic Carbene

et al. 2010

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“…Cyclic sulfamidates are valuable reactive intermediates, because ring-opening reactions proceed with total inversion at the stereogenic centre (Melé ndez & Lubell, 2003). The title compound represents such a building block derived from (R)-1-amino-2-propanol useful for the preparation of substituted -phenylethylamines, an important class of pharmacologically active compounds (Hebeisen et al, 2011).…”

Section: Structure Descriptionmentioning

confidence: 99%

(R)-3-(tert-Butoxycarbonyl)-5-methyl-1,2,3-oxathiazolidine 2,2-dioxide

et al. 2017

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The chiral title compound, C 8 H 15 NO 5 S, was obtained by cyclization of (R)-1-(tert-butoxycarbonylamino)-2-propanol with thionyl chloride and subsequent oxidation with sodium metaperiodate/ruthenium(IV) oxide. It crystallizes with two independent molecules in the asymmetric unit. In the crystal, C-HÁ Á ÁO interactions link the molecules into a three-dimensional network. Structure descriptionCyclic sulfamidates are valuable reactive intermediates, because ring-opening reactions proceed with total inversion at the stereogenic centre (Melé ndez & Lubell, 2003). The title compound represents such a building block derived from (R)-1-amino-2-propanol useful for the preparation of substituted -phenylethylamines, an important class of pharmacologically active compounds (Hebeisen et al., 2011). The configuration of the enantiomer has been assigned by reference to an unchanging chiral centre in the synthetic procedure and confirmed by anomalous-dispersion effects in diffraction measurements on the crystal: the Flack parameter was refined to 0.02 (2).The title compound crystallizes with two independent molecules in the asymmetric unit. The five-membered rings adopt (O)C-envelope conformations, denoting the flap atoms, C1 and C6, are adjacent to the oxygen atoms. The methyl groups occupy equatorial positions (Fig. 1). The bonding geometries at the N atoms are close to planar, as the sums of the angles at N1 and N2 are 358.9 and 358.8 , respectively, and the N atoms lie only 0.092 and 0.094 Å out of the planes of the atoms to which they are bonded, as expected for an N-acyl fragment. In the crystal, C-HÁ Á ÁO interactions (Table 1) are observed. The apolar tert-butyl groups and the polar sulfamidate rings are alternately arranged in layers parallel to the bc-plane (Fig. 2).

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Synthesis and reactivity of cyclic sulfamidites and sulfamidates

Cited by 193 publications

References 60 publications

Rhodium(II)‐Catalyzed Oxidative Amination

Rhodium(II)‐Catalyzed Oxidative Amination

Highly Active Chiral Ruthenium‐Based Metathesis Catalysts through a Monosubstitution in the N‐Heterocyclic Carbene

(R)-3-(tert-Butoxycarbonyl)-5-methyl-1,2,3-oxathiazolidine 2,2-dioxide

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