@article {49507,
	title = {Studies on the stereoselective synthesis of sacubitril via a chiral amine transfer approach},
	journal = {Chemistry-An Asian Journal},
	volume = {20},
	year = {2025},
	month = {MAR },
	type = {Article},
	abstract = {<p>
	We present a comprehensive account of our efforts directed towards the synthesis of sacubitril, a neprilysin inhibitor used in combination with valsartan and marketed as Entresto (TM). Our initial approach to the formal synthesis of sacubitril employed a chiral pool strategy, utilizing (S)-pyroglutamic acid as a key building block and Cu(I)-mediated Csp2-Csp3 cross-coupling as a key transformation. Further investigations led to the development of chiral amine transfer (CAT) reagents-based stereoselective synthesis. This involved the E-selective construction of gamma-ylidene-butenolide from readily available biphenyl bromide and 4-pentynoic acid, the conversion of this butenolide to its ene-lactam using chiral amine, and substrate-controlled diastereoselective reduction of ene-lactam using Et3SiH or Pd/C, H2 (overall chiral amine transfer) as key transformations. Antipodal lactam intermediates were synthesized using corresponding chiral amines, and the stereochemical outcomes during the ene-lactam reduction with Et3SiH were rationalized by DFT studies.</p>
},
	keywords = {Chiral Amine Transfer (CAT) approach, Chiral pool approach, Sacubitril, stereoselective synthesis},
	issn = {1861-4728},
	doi = {10.1002/asia.202401223},
	author = {Sadanande, Megha V. and Thorat, Sagar S. and Sharma, Himanshu and Singh, Geetika and Vanka, Kumar and Gonnade, Rajesh G. and Kontham, Ravindar}
}
@article {50089,
	title = {Divergent synthesis of meyers{\textquoteright} lactams and medium lactams via cyclocondensation of γ-ylidene-butanolides with chiral amino alcohols},
	journal = {Journal of Organic Chemistry},
	volume = {91},
	year = {2026},
	month = {APR},
	pages = {5138-5158},
	type = {Article},
	abstract = {<p>
	A novel methodology for constructing Meyers{\textquoteright} lactams (pyrrolidino-oxazolidines), related to biologically potent natural and synthetic scaffolds, has been developed via an unprecedented tandem cyclocondensation of chiral 2-amino alcohols and gamma-ylidene-butanolides. The process proceeds through the initial formation of an ene-lactam intermediate, followed by a Bro/nsted acid (PPTS)-catalyzed ring closure. Under stoichiometric amounts of a Lewis acid (TiCl4), the same set of building blocks affords medium lactams featuring eight-membered ring systems with an exo-enol ether segment. This divergent synthetic strategy enables the efficient generation of a library of Meyers{\textquoteright} lactams and medium lactams with good yields and diastereoselectivity.</p>
},
	issn = {0022-3263},
	doi = {10.1021/acs.joc.6c00086},
	author = {Sadanande, Megha V. and Sharma, Paridhi and Gonnade, Rajesh G. and Kontham, Ravindar}
}
