215930-48-6

Upstream product

• 156764-21-5 3,4-di-O-benzyl-1,6-di-O-toluenesulfonyl-D-mannitol 
• 69-65-8 mannitol 
• 1707-77-3 1,2:5,6-di-O-isopropylidene-D-mannitol 
• 111476-62-1 3,4-di-O-benzyl-1,2:5,6-di-O-isopropylidene-D-mannitol 
• 36199-02-7 3,4-di-O-benzyl-D-mannitol 

Downstream Products

• 215930-44-2 1,2-bis((4S,5S,6S,7S)-5,6-dibenzyloxy-4,7-dimethylphospholanyl)-benzene 
• 259752-07-3 (2S,3S,4S,5S)-3,4-dibenzyloxy-2,5-Me₂-1-phenylphospholane 
• 215930-49-7 (4R,5S,6S,7R)-5,6-Bis-benzyloxy-4,7-dimethyl-[1,3,2]dioxathiepane 2,2-dioxide 

Relevant academic research and scientific papers

Asymmetric hydrogenation of β-keto esters

Enantiomerically pure β-hydroxy esters are prepared by a process in which β-keto esters are reacted with hydrogen in the presence of catalysts of the formula LRuX2where X is halogen, acetate, allyl, methallyl, 2-phenylallyl, perchlorate, trifluoroacetate, tetrafluoroborate, hexafluoroantimonate, hexafluorophosphate, hexafluoroarsenate or trichloroacetate, L is a bidentate phospholane of the formula I ?where B=a bridging link with 1-5 carbon atoms between the two phosphorus atoms, R1=H, C1-C6-alkyl, aryl, alkylaryl or SiR23, R2=alkyl or aryl, m=0 or 1, R3=H or OR4, and R4=R1, with the proviso that if m=1 then R3=H and if m=0 then R3≠ H.

Preparation of optically active phospholanes, their metal complexes and use in asymmetric synthesis

Phospholanes and diphospholanes of the formula I where: R1 and R2 are, independently of one another, C1-C6-alkyl, aryl, alkylaryl, R1 is also hydrogen, A is either R1 or B is a linker having 1-5 carbon atoms between the two phosphorus atoms, and their use

Synthesis of chiral hydroxyl phospholanes from D-mannitol and their use in asymmetric catalytic reactions

Chiral hydroxyl monophosphane 3 [(2S,3S,4S,5S)-3,4-dihydroxy-2,5-dimethyl-1-phenylphospholane] and bisphospholanes 5a [1,2-bis[(2S,3S,4S,5S)-3,4-dihydroxy-2,5-dimethylphospholanyl]benzene] and 5b [1,2-bis[(2S,3S,4S,5S)-2,5-diethyl-3,4-dihydroxyphospholanyl]benzene] were synthesized from readily available D-mannitol in high yields. Strategies for protection and deprotection of OH-groups in the presence of phosphines have been explored. Rate acceleration in the Baylis - Hillman reaction was observed when a hydroxyl phosphine was used as the catalyst. Rhodium complexes with chiral bisphospholanes are highly enantioselective catalysts for the asymmetric hydrogenation of various kinds of functionalized olefins such as dehydroamino acid derivatives, itaconic acid derivatives, and enamides. An interesting feature of the hydroxyl phospholane system is that hydrogenation of some substrates can be carried out in water with >99% ee and 100% conversion (e.g., itaconic acid).