Hu, Shaojing published the artcileDiastereoselective chloroallylboration of α-chiral aldehydes, Category: ethers-buliding-blocks, the publication is Journal of Organic Chemistry (1998), 63(24), 8843-8849, database is CAplus.
Double asym. reaction of chiral (Z)-(γ-chloroallyl)diisopinocampheylboranes, d-I and l-I, with α-chiral aldehydes (S)-MeCH2CHMeCHO, N-Boc-L-valinal (II), (R)-2,3-O-isopropylidnene-D-glyceraldehyde, and (R)- and (S)-Me3CSiMe2OCH2CHMeCHO provide a new practical method for the generation of 2,3-syn-3,4-anti and 2,3-syn-3,4-syn chiral vinylchlorohydrins and vinyl epoxides. Both enantiomers d-I and l-I exhibited excellent diastereoselectivity (≥90 de) for matched cases. The mismatched cases yielded moderate to good diastereoselectivity. Thus, l-I was generated in situ from allyl chloride and l-B-methoxydiisopinocampheylborane by treatment with Li dicyclohexylamide and F3B.OEt2 in Et2O/THF and reacted with II at -95° for four hours to give 60% of 99:1 mixture of vinyl chlorohydrins III and IV. Similar reaction of II with d-I gave 61% of a 15:85 mixture of III and IV. Cyclization of III in MeOH containing K2CO3 gave 98% vinyloxirane V.
Journal of Organic Chemistry published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Category: ethers-buliding-blocks.
Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem