And second, you're dismissing the fact that TypeScript is unsound, even worse it is so by design. Easy examples: uninitialized variables holding undefined when their type says they can't [1]; array covariance [2]; and function parameter bivariance, which is part of the TypeScript playground's own example on soundness issues [3] but at least this one can be configured away.
C# and Java made the same mistake of array covariance, but they have the decency of checking for it at runtime.
[1]: https://www.typescriptlang.org/play/?#code/DYUwLgBAHgXBB2BXA... [2]: https://www.typescriptlang.org/play/?#code/MYewdgzgLgBAllApg... [3]: https://www.typescriptlang.org/play/?strictFunctionTypes=fal...
As for your example, I agree that TypeScript unions and singleton types are powerful, but I can't see what are you speficially missing here that pattern matching and maybe an additional variant type doesn't get you in OCaml. You get exhaustiveness checking and can narrow the value down to the payload of the variant.