diff --git a/databind/src/databind/json/converters.py b/databind/src/databind/json/converters.py
index 18b8488..80013ea 100644
--- a/databind/src/databind/json/converters.py
+++ b/databind/src/databind/json/converters.py
@@ -763,20 +763,39 @@ def _check_style_compatibility(self, ctx: Context, style: str, value: t.Any) ->
     def convert(self, ctx: Context) -> t.Any:
         datatype = ctx.datatype
         union: t.Optional[Union]
-        literal_types: list[TypeHint] = []
 
         if isinstance(datatype, UnionTypeHint):
             if datatype.has_none_type():
                 raise NotImplementedError("unable to handle Union type with None in it")
 
-            literal_types = [a for a in datatype if isinstance(a, LiteralTypeHint)]
+            literal_values = [
+                literal_value
+                for literal_type in datatype
+                if isinstance(literal_type, LiteralTypeHint)
+                for literal_value in literal_type.values
+            ]
+
+            literal_type: t.Optional[TypeHint] = None
+            if literal_values:
+                literal_type = t.Literal[tuple(literal_values)]  # type: ignore
+
             non_literal_types = [a for a in datatype if not isinstance(a, LiteralTypeHint)]
             if not all(isinstance(a, ClassTypeHint) for a in non_literal_types):
                 raise NotImplementedError(f"members of plain Union must be concrete or Literal types: {datatype}")
 
             members = {t.cast(ClassTypeHint, a).type.__name__: a for a in non_literal_types}
             if len(members) != len(non_literal_types):
-                raise NotImplementedError(f"members of plain Union cannot have overlapping type names: {datatype}")
+                raise ConversionError(
+                    self, ctx, f"members of plain Union cannot have overlapping type names: {datatype}"
+                )
+
+            if literal_type is not None:
+                if "Literal" in members:
+                    raise ConversionError(
+                        self, ctx, f"members of plain Union with a Literal cannot have type name Literal: {datatype}"
+                    )
+                members["Literal"] = literal_type
+
             union = Union(members, Union.BEST_MATCH)
         elif isinstance(datatype, (AnnotatedTypeHint, ClassTypeHint)):
             union = ctx.get_setting(Union)
@@ -794,11 +813,6 @@ def convert(self, ctx: Context) -> t.Any:
                     return ctx.spawn(ctx.value, member_type, None).convert()
                 except ConversionError as exc:
                     errors.append((exc.origin, exc))
-            for literal_type in literal_types:
-                try:
-                    return ctx.spawn(ctx.value, literal_type, None).convert()
-                except ConversionError as exc:
-                    errors.append((exc.origin, exc))
             raise ConversionError(
                 self,
                 ctx,