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A Highly Diastereoselective TiCl 4 ‐Mediated Reduction of β‐Hydroxy Ketones with BH 3 ·py — A Very Efficient and General Synthesis of syn ‐1,3‐Diols
Author(s) -
Bartoli Giuseppe,
Bosco Marcella,
Marcantoni Enrico,
Massaccesi Massimo,
Rinaldi Samuele,
Sambri Letizia
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200112)2001:24<4679::aid-ejoc4679>3.0.co;2-o
Subject(s) - chemistry , alkyl , pyridine , bromide , nitro , medicinal chemistry , primary (astronomy) , diol , organic chemistry , stereochemistry , physics , astronomy
β‐Hydroxy ketones can be reduced to the corresponding 1,3‐diols in high yields and with excellent diastereoselectivity by carrying out the reaction with BH 3 ·pyridine in CH 2 Cl 2 at −78 °C in the presence of TiCl 4 . This protocol is general and chemoselective: excellent results are obtained when the substituents are primary, secondary, tertiary alkyl chains or aromatic moieties. The presence of reducible functionalities such as bromide, nitro and cyano groups is well tolerated.