A comparison of 1 vs. propyne BMIDA (7) revealed static rhodium turnover (RTO) for 7 irrespective of catalyst loading, consistent with the sterically controlled regime; 56 however, despite the same steric parameters, 1 displayed enhanced turnover due to chelation assistance. Interestingly, assessment of 6 revealed a similar but slightly diminished chelation assistance despite the presence of the TBS protecting group. This proved advantageous for method development: while 1 could be prepared and isolated, the stability of the neat material was poor, requiring use immediately. Alkyne 6 had no stability issues and therefore offered a complementary approach to the BOB framework using the same number of overall steps by incorporating TBS deprotection either as work-up after cycloaddition or after purification of the aryl BMIDA (vide infra).