A Concise Stereoselective Route to <i>C‐</i> and <i>P</i>‐ Chirogenic Hydroxypropyl Phosphines by Ring‐Opening of Optically Active Oxaphospholane‐2‐oxide

Keisar, Orit Redy; Ashkenazi, Nissan

doi:10.1002/slct.201803804

Cited by 3 publications

(2 citation statements)

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“…(S)-2-Phenyl-1,2-oxaphospholane 177 was prepared from (S)-3-bromo-2-methylpropan-1-ol (176) and dimethyl phenylphosphonite via tandem Arbuzov reaction and transesterification and further applied in the ring-opening reaction and alkylation (Scheme 45). [69] A heptanose-fused 1,2-oxaphospholane 2-oxide 179 was synthesized in 80 % yield from partial benzyl-protected 1iodomethylheptanose 178 and triethyl phosphite via the Arbuzov reaction and subsequent transesterification (Scheme 46). [70]…”

Section: [4 + 1] Annulation Via the Arbuzov Reaction And Transesterif...mentioning

confidence: 99%

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Syntheses of 1,2‐Oxaphospholane 2‐Oxides and 1,2‐Oxaphosphole 2‐Oxides

2023

ChemistrySelect

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1,2‐Oxaphospholane and 1,2‐oxaphosphole 2‐oxides, γ‐phosphonolactones and γ‐phosphinolactones, also called γ‐phostones and γ‐phostines, are important five‐membered 1,2‐oxaphosphaheterocycles and crucial motifs of some biologically active compounds. Various synthetic methods of these 1,2‐oxaphosphaheterocycles have been developed till now. They can be divided as cyclization, annulation, cycloaddition, ring expansion and contractions. The cyclizations mainly include intramolecular nucleophilic substitution of 3‐haloalkylphosphonic and phosphinic acid derivatives, esterification of 3‐hydroxyalkylphosphonic/phosphinic acids, transesterification of alkyl 3‐hydroxyalkylphosphonates/phosphinates, halocyclization of alkyl alk‐2/3‐enylphosphonates, halocyclization of allenylphosphonic acid derivatives, the transition metal‐catalyzed oxidative cyclizations of benzyl/2‐methylphenylphosphonic/phosphinic acids, and the Pd‐catalyzed cyclization of γ‐bromoalkyl phosphonates/phosphinates. The annulations covers [4+1] and [3+2] annulations. In this review, we have described various strategies and further development for the synthesis of 1,2‐oxaphospholane and 1,2‐oxaphosphole 2‐oxides.

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Section: [4 + 1] Annulation Via the Arbuzov Reaction And Transesterif...mentioning

confidence: 99%

“…( S )‐2‐Phenyl‐1,2‐oxaphospholane 177 was prepared from ( S )‐3‐bromo‐2‐methylpropan‐1‐ol ( 176 ) and dimethyl phenylphosphonite via tandem Arbuzov reaction and transesterification and further applied in the ring‐opening reaction and alkylation (Scheme 45). [69] …”

Section: Synthesis Through Annulationmentioning

confidence: 99%

Syntheses of 1,2‐Oxaphospholane 2‐Oxides and 1,2‐Oxaphosphole 2‐Oxides

2023

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An iron variant of the Noyori hydrogenation catalyst for the asymmetric transfer hydrogenation of ketones

2020

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Two-Step Substitution Reaction of Phosphonates Carrying a Binaphthyl Group with Grignard Reagents Leading to the Formation of P-Chirogenic Phosphine Oxides

Ono

Sugiyama

Sakamoto

et al. 2022

Synlett

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The reaction of phosphonates with a binaphthyl group with a range of Grignard reagents was complete within 2 h at 0 °C to give phosphinates with a hydroxybinaphthyl group with high efficiency and diastereoselectivity. The resulting phosphinates were further subjected to the substitution reaction with MeMgBr. The reaction at reflux temperature in THF or toluene enabled the formation of P-chirogenic tertiary phosphine oxides with a high enantiomeric ratio. Rare examples of P-chirogenic alkynyl phosphine oxides were also obtained. The sequential one-pot substitution reaction of phosphonates with a binaphthyl group with two different Grignard reagents successfully gave the corresponding P-chirogenic phosphine oxides with an enantiomeric ratio nearly equal to those of oxides derived from two-step reactions.

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A Concise Stereoselective Route to C‐ and P‐ Chirogenic Hydroxypropyl Phosphines by Ring‐Opening of Optically Active Oxaphospholane‐2‐oxide

Cited by 3 publications

References 54 publications

Syntheses of 1,2‐Oxaphospholane 2‐Oxides and 1,2‐Oxaphosphole 2‐Oxides

Syntheses of 1,2‐Oxaphospholane 2‐Oxides and 1,2‐Oxaphosphole 2‐Oxides

An iron variant of the Noyori hydrogenation catalyst for the asymmetric transfer hydrogenation of ketones

Two-Step Substitution Reaction of Phosphonates Carrying a Binaphthyl Group with Grignard Reagents Leading to the Formation of P-Chirogenic Phosphine Oxides

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