ChemInform Abstract: Large‐Scale Preparation of α,α,α′,α′‐Tetraaryl‐ 1,3‐dioxolane‐4,5‐dimethanols (TADDOLs): Versatile Auxiliaries for EPC‐ Synthesis and Their Solid‐State Structure.

Beck, Albert K.; Bastani, Bahram; Plattner, Dietmar A.; Petter, W.; Seebàch, Dieter; Braunschweiger, H.; Gysi, Peter; Vecchia, Luigi La

doi:10.1002/chin.199229163

Cited by 13 publications

(15 citation statements)

References 1 publication

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“…Synthesized from (+)‐dimethyl ( R , R )‐ l ‐tartrate (8.92 g, 50 mmol) according to a literature procedure in 87 % yield (8.26 g, 43.4 mmol) . The analytical data matched previously published values . 1 H NMR (400.1 MHz, CDCl 3 ): δ = 3.81 (s, 6H), 4.75 (s, 2H), 5.24 (s, 2H).…”

Section: Methodssupporting

confidence: 68%

Synthesis of α,ω‐Bis‐Enones by the Double Addition of Alkenyl Grignard Reagents to Diacid Weinreb Amides

et al. 2019

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An efficient double addition of substituted alkenylmagnesium bromides to bis‐Weinreb amides has been developed, giving α,ω‐bis‐enones that are building blocks for certain drugs and polymers. Furthermore, reliable protocols for the preparation of the required substituted alkenylmagnesium reagents from substituted non‐activated alkenyl bromides are reported. The double addition is demonstrated on 25 examples, including enantiopure as well as conjugated and cross‐conjugated bis‐enones. The addition to a cyclohexane‐1,2‐dicarboxamide was found to lead to a selective mono addition, giving access to cyclohexyl γ‐ketoamides that are core motifs of several pharmaceutical agents and promising drug candidates.

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Section: Methodssupporting

confidence: 68%

Synthesis of α,ω‐Bis‐Enones by the Double Addition of Alkenyl Grignard Reagents to Diacid Weinreb Amides

et al. 2019

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“…1‐ n ‐Butyl‐3‐methyl‐3‐phospholene 1‐oxide ( 1 ), (−)‐(4 R ,5 R )‐4,5‐bis(diphenylhydroxymethyl)‐2,2‐dimethyldioxolane [(−)‐ 2 ], (−)‐(2 R ,3 R )‐α,α,α',α'‐tetraphenyl‐1,4‐dioxaspiro[4.5]decan‐2,3‐dimethanol [(−)‐ 3 ] and calcium hydrogen (−)‐ O , O '‐dibezoyl‐(2 R ,3 R )‐tartrate [(−)‐ 4 ] were synthesized as described earlier. (−)‐ O , O '‐Dibezoyl‐ and (−)‐ O , O '‐di‐ p ‐toluoyl‐(2 R ,3 R )‐tartaric acid were purchased from Aldrich Chemical (Milwaukee, WI).…”

Section: Methodsmentioning

confidence: 99%

Resolution of 1‐n‐Butyl‐3‐Methyl‐3‐Phospholene 1‐Oxide With TADDOL Derivatives and Calcium Salts of O,O'‐Dibenzoyl‐(2R,3R)‐ or O,O'‐di‐p‐Toluoyl‐(2R,3R)‐tartaric Acid

et al. 2014

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The resolution methods applying (-)-(4R,5R)-4,5-bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane ("TADDOL"), (-)-(2R,3R)-α,α,α',α'-tetraphenyl-1,4-dioxaspiro[4.5]decan-2,3-dimethanol ("spiro-TADDOL"), as well as the acidic and neutral Ca(2+) salts of (-)-O,O'-dibenzoyl- and (-)-O,O'-di-p-toluoyl-(2R,3R)-tartaric acid were extended for the preparation of 1-n-butyl-3-methyl-3-phospholene 1-oxide in optically active form. In one case, the intermediate diastereomeric complex could be identified by single-crystal X-ray analysis. The absolute P-configuration of the enantiomers of the phospholene oxide was also determined by comparing the experimentally obtained and calculated CD spectra.

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“…The (−)-(4R,5R)-4,5-bis(diphenylhydroxymethyl)-2,2dimethyldioxolane [(−)-4], (−)-(2R,3R)-α,α,α′,α′-tetraphenyl-1,4-dioxaspiro[4.5]decan-2,3-dimethanol [(−)-5] were synthesized as described earlier. 66 The (−)-O,O′-dibenzoyland (−)-O,O′-di-p-toluoyl-(2R,3R)-tartaric acid were purchased from Sigma Aldrich.…”

Section: General (Instruments)mentioning

confidence: 99%

The resolution of acyclic P‐stereogenic phosphine oxides via the formation of diastereomeric complexes: A case study on ethyl‐(2‐methylphenyl)‐phenylphosphine oxide

et al. 2018

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As an example of acyclic P-chiral phosphine oxides, the resolution of ethyl-(2-methylphenyl)-phenylphosphine oxide was elaborated with TADDOL derivatives, or with calcium salts of the tartaric acid derivatives. Besides the study on the resolving agents, several purification methods were developed in order to prepare enantiopure ethyl-(2-methylphenyl)-phenylphosphine oxide. It was found that the title phosphine oxide is a racemic crystal-forming compound, and the recrystallization of the enantiomeric mixtures could be used for the preparation of pure enantiomers. According to our best method, the (R)-ethyl-(2-methylphenyl)-phenylphosphine oxide could be obtained with an enantiomeric excess of 99% and in a yield of 47%. Complete racemization of the enantiomerically enriched phosphine oxide could be accomplished via the formation of a chlorophosphonium salt. Characterization of the crystal structures of the enantiopure phosphine oxide was complemented with that of the diastereomeric intermediate. X-ray analysis revealed the main nonbonding interactions responsible for enantiomeric recognition.

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ChemInform Abstract: Large‐Scale Preparation of α,α,α′,α′‐Tetraaryl‐ 1,3‐dioxolane‐4,5‐dimethanols (TADDOLs): Versatile Auxiliaries for EPC‐ Synthesis and Their Solid‐State Structure.

Cited by 13 publications

References 1 publication

Synthesis of α,ω‐Bis‐Enones by the Double Addition of Alkenyl Grignard Reagents to Diacid Weinreb Amides

Synthesis of α,ω‐Bis‐Enones by the Double Addition of Alkenyl Grignard Reagents to Diacid Weinreb Amides

Resolution of 1‐n‐Butyl‐3‐Methyl‐3‐Phospholene 1‐Oxide With TADDOL Derivatives and Calcium Salts of O,O'‐Dibenzoyl‐(2R,3R)‐ or O,O'‐di‐p‐Toluoyl‐(2R,3R)‐tartaric Acid

The resolution of acyclic P‐stereogenic phosphine oxides via the formation of diastereomeric complexes: A case study on ethyl‐(2‐methylphenyl)‐phenylphosphine oxide

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