The Hosomi–Sakurai reaction has received enormous attention since its inception and will continue to do so, owing to its atom-economical carbon–carbon bond forming ability. The remarkable feature of this reaction is the use of simple achiral starting materials which leads to the product having a chiral carbon centre with two active functionalities which serve as the guiding stone towards easy synthesis of natural products/bioactive heterocyclic scaffolds/drug candidates. The journey which started with the use of stoichiometric amounts of catalyst has now reached catalytic quantity and that too with economical and ecological aspects. In this review we have emphasized on this journey with regard to Lewis acids, metal triflates, Brønsted acids, heterogeneous catalysts and easily available inexpensive catalysts such as iodine. Our objective is to brief the readers with in-depth knowledge on the development and recent trends in the use of novel catalysts so as to provoke research in this fascinating and enormously useful area which will lead to the development of environmentally benign and economically viable protocols to a greater extent.