tmds ( 2.0  equiv ) and [ ircl(co)(pph3)2 ] ( 0.005  equiv ) were added to a stirred solution of nitro - lactam 3 ( 1.0  equiv ) in toluene ( 0.01  m ) under an inert atmosphere at room temperature . the resulting solution was stirred for 10  mins until complete conversion of the starting material was observed ( tlc ) , and then quenched with 1  m hcl ( 12  ml  mmol 
 3 ) . the aqueous layer was separated and the organic layer was extracted ( 1  m hcl , 312  ml  mmol 
 3 ) . the combined aqueous extracts were washed ( et2o , 36  ml  mmol 
 3 ) and basified to ph>10 ( k2co3 ) . the aqueous layer was then extracted ( et2o , 36  ml  mmol 
 3 ) , and the organic phases combined , dried ( mgso4 ) , filtered and concentrated in vacuo . as a service to our authors and readers , this journal provides supporting information supplied by the authors . such materials are peer reviewed and may be re - organized for online delivery , but are not copy - edited or typeset . technical support issues arising from supporting information ( other than missing files ) should be addressed to the authors
a new chemoselective reductive nitro - mannich cyclization reaction sequence of nitroalkyl - tethered lactams has been developed . 
 relying on the rapid and chemoselective iridium(i)-catalyzed reduction of lactams to the corresponding enamine , subsequent nitro - mannich cyclization of tethered nitroalkyl functionality provides direct access to important alkaloid natural - product - like structures in yields up to 81  % and in diastereoselectivities that are typically good to excellent . 
 an in - depth understanding of the reaction mechanism has been gained through nmr studies and characterization of reaction intermediates . 
 the new methodology has been applied to the total synthesis of ( )-epi - epiquinamide in four steps .